Category: 286454-86-2

The author of 《Tunable Bifunctional Phosphine-Squaramide Promoted Morita-Baylis-Hillman Reaction of N-Alkyl Isatins with Acrylates》 were Dong, Ze; Yan, Chao; Gao, Yongzhi; Dong, Chune; Qiu, Guofu; Zhou, Hai-Bing. And the article was published in Advanced Synthesis & Catalysis in 2015. Recommanded Product: (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine The author mentioned the following in the article:

A series of highly tunable bifunctional phosphine-squaramide H-bond donor organocatalysts I (R1 = i-Pr, Ph, t-Bu; R2 = 4-FC6H4, 3,5-(CF3)2C6H3, 3,5-(CF3)2C6H3CH2) has been synthesized from inexpensive and com. available β-amino alcs. in moderate yields. Catalyst I (R1 = t-Bu; R2 = 3,5-(CF3)2C6H3) can efficiently promote the asym. Morita-Baylis-Hillman (MBH) reaction of N-alkyl isatins with acrylate esters providing the chiral 3-substituted 3-hydroxy-2-oxindoles II (R3 = H, 4-Br, 5-F, etc.; R4 = Me, i-Pr, allyl, Bn, etc.; R5 = Me, Et, Bu, t-Bu) in good yields and enantioselectivities (up to 93 % yield and 95 % ee), in which the challenging substrate tert-Bu acrylate tert-Bu prop-2-enoate, provided the best ee value to date. This methodol. was applied successfully in the synthesis of chiral cyclic spiropyrrolizidineoxindole and γ-butyrolactone derivatives without enantioselectivity deterioration. The KIE experiments show that the electrophilic addition of N-Me isatin to the complex of acrylate ester and phophine-squaramide is the rate-determining step of the asym. MBH reaction. After reading the article, we found that the author used (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas: 286454-86-2Recommanded Product: (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine)

(S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas:286454-86-2) is one of aminophosphine type ligands. An increased interest in aminophosphine type ligands used for asymmetric synthesis has been witnessed.Recommanded Product: (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine This growth in popularity of aminophosphine ligands in asymmetric synthesis is in part due to the growing number of convenient synthetic pathways leading to useful ligand sets.

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Application of 286454-86-2On March 17, 2017, Su, Hsin Y.; Taylor, Mark S. published an article in Journal of Organic Chemistry. The article was 《P-Stereogenic β-aminophosphines: preparation and applications in enantioselective organocatalysis》. The article mentions the following:

The synthesis of stereodefined β-aminophosphines ArPhPCH2CH(tBu)NH2 (1a,b, Ar = 2-MeOC6H4) having both carbon- and phosphorus-based chirality centers is described. The method involves resolution of a mixture of β-aminophosphine oxide diastereomers accessed by ring-opening of an amino alc.-derived cyclic sulfamidate. A stereospecific, borane-promoted reduction of β-aminophosphine oxides, which occurs under mild conditions and with inversion of configuration at phosphorus, is a key step in this process. The products obtained are new building blocks for the synthesis of P-chiral ligands and organocatalysts. In a proof-of-concept application in organocatalysis, the diastereomeric P-chiral β-aminophosphine-based bifunctional thioureas displayed significantly different activities in the Morita-Baylis-Hillman reaction of Me acrylate with benzaldehyde derivatives In the experiment, the researchers used many compounds, for example, (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas: 286454-86-2Application of 286454-86-2)

(S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas:286454-86-2) is one of aminophosphine type ligands. An increased interest in aminophosphine type ligands used for asymmetric synthesis has been witnessed.Application of 286454-86-2 This growth in popularity of aminophosphine ligands in asymmetric synthesis is in part due to the growing number of convenient synthetic pathways leading to useful ligand sets.

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Guo, Rongwei; Lu, Shuiming; Chen, Xuanhua; Tsang, Chi-Wing; Jia, Wenli; Sui-Seng, Christine; Amoroso, Dino; Abdur-Rashid, Kamaluddin published an article on February 5 ,2010. The article was titled 《Synthesis of Chiral Aminophosphines from Chiral Aminoalcohols via Cyclic Sulfamidates》, and you may find the article in Journal of Organic Chemistry.Synthetic Route of C18H24NP The information in the text is summarized as follows:

Protic aminophosphines with multiple chiral centers were synthesized in good yields and high purity by the nucleophilic ring-opening of N-protected cyclic sulfamidates with metal phosphides, followed by hydrolysis and deprotection. This synthetic approach is clean, scalable, and high yielding. The method provides an efficient alternative route for the synthesis of chiral aminophosphines. In the experiment, the researchers used (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas: 286454-86-2Synthetic Route of C18H24NP)

(S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas:286454-86-2) is one of aminophosphine type ligands. An increased interest in aminophosphine type ligands used for asymmetric synthesis has been witnessed.Synthetic Route of C18H24NP This growth in popularity of aminophosphine ligands in asymmetric synthesis is in part due to the growing number of convenient synthetic pathways leading to useful ligand sets.

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

In 2019,Organic & Biomolecular Chemistry included an article by Wang, Kaiye; Xiang, Yanan; Shi, Zhujun; Wang, Hongyu; Li, Na; Tang, Bo. Reference of (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine. The article was titled 《Asymmetric kinetic resolution of sulfides for the construction of unsymmetric sulfides and chiral 3,3-disubstituted oxindoles》. The information in the text is summarized as follows:

An enantioselective method was developed for the synthesis of unsym. disulfides R’SSR” [R’ = allyl, CH2CO2Me, Bn, etc.; R” = 4-FC6H4, 4-BrC6H4, Bn] and chiral 3,3-disubstituted oxindoles I [R1 = allyl, 4-BrC6H4, Bn, etc.; X = H, 5-Br, 5-I, 6-Br; R2 = Me, PMB] in one step from oxindoles and thiols using chiral phosphines catalyst. Many substituted thiols and 3,3-disubstituted oxindoles were well tolerated and produced high yields and enantioselectivities under mild conditions. In the experimental materials used by the author, we found (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas: 286454-86-2Reference of (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine)

(S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas:286454-86-2) is one of aminophosphine type ligands. An increased interest in aminophosphine type ligands used for asymmetric synthesis has been witnessed.Reference of (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine This growth in popularity of aminophosphine ligands in asymmetric synthesis is in part due to the growing number of convenient synthetic pathways leading to useful ligand sets.

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Saitoh, Akihito; Achiwa, Kazuo; Tanaka, Kiyoshi; Morimoto, Toshiaki published an article in Journal of Organic Chemistry. The title of the article was 《Versatile Chiral Bidentate Ligands Derived from α-Amino Acids: Synthetic Applications and Mechanistic Considerations in the Palladium-Mediated Asymmetric Allylic Substitutions》.HPLC of Formula: 286454-86-2 The author mentioned the following in the article:

A new class of chiral amidine-phosphine hybrid ligands which are readily accessible from the corresponding α-amino acids was developed. A versatility for construction of new ligands is desirable, by which a variety of reactions and substrates become applicable. Indeed, a variety of modifications, such as exchange reactions to other amino groups in the amidine skeleton and the production of other types of ligands, are possible using the precursor compounds Thus, novel chiral ligands which provide sterically and electronically different chiral circumstances were prepared and used for the palladium-mediated asym. allylic substitutions of both acyclic and cyclic compounds In these reactions, high levels of asym. induction were achieved for both substrates. A marked advancement of reactivity and enantioselectivity in palladium-catalyzed asym. allylations of 1,3-diphenylpropen-2-yl pivalate (14a) was attained by examination of electronic substituent effects in a new series of chiral P-N and S-N hybrid ligands. Mechanistic views concerning the enantiodiscriminating step were demonstrated, in which a good correlation between a novel Pr/Mr concept and the absolute configuration of allylation products are discussed for the prediction of enantioselecting direction. The use of ketene silyl acetals as nucleophiles was investigated and compared with the corresponding harder anionic carbon nucleophiles. The former nucleophiles afforded higher enantioselectivity in asym. allylic transformations of 14a. The experimental part of the paper was very detailed, including the reaction process of (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas: 286454-86-2HPLC of Formula: 286454-86-2)

(S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas:286454-86-2) is one of aminophosphine type ligands. An increased interest in aminophosphine type ligands used for asymmetric synthesis has been witnessed.HPLC of Formula: 286454-86-2 This growth in popularity of aminophosphine ligands in asymmetric synthesis is in part due to the growing number of convenient synthetic pathways leading to useful ligand sets.

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

《Asymmetric [3+2] Cycloadditions of Allenoates and Dual Activated Olefins Catalyzed by Simple Bifunctional N-Acyl Aminophosphines》 was published in Angewandte Chemie, International Edition in 2010. These research results belong to Xiao, Hua; Chai, Zhuo; Zheng, Chang-Wu; Yang, Ying-Quan; Liu, Wen; Zhang, Jun-Kang; Zhao, Gang. SDS of cas: 286454-86-2 The article mentions the following:

Chiral cyclopentene derivatives, e.g. I, were prepared via asym. organocatalytic [3+2] cycloaddition between allenoates, e.g. CH2:C:CHCO2Et, and dual activated olefin, e.g. II, using bifunctional N-acylaminophosphine catalysts, e.g. III.(S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas: 286454-86-2SDS of cas: 286454-86-2) was used in this study.

(S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas:286454-86-2) is one of aminophosphine type ligands. An increased interest in aminophosphine type ligands used for asymmetric synthesis has been witnessed.SDS of cas: 286454-86-2 This growth in popularity of aminophosphine ligands in asymmetric synthesis is in part due to the growing number of convenient synthetic pathways leading to useful ligand sets.

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Mato, Raquel; Manzano, Ruben; Reyes, Efraim; Carrillo, Luisa; Uria, Uxue; Vicario, Jose L. published an article in Journal of the American Chemical Society. The title of the article was 《Catalytic Enantioselective Transannular Morita-Baylis-Hillman Reaction》.Name: (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine The author mentioned the following in the article:

Catalytic and enantioselective approaches to transannular reactions are very limited and mostly are based on chiral Lewis acid catalyzed pericyclic reactions. The authors present an efficient and straightforward methodol. to access bicyclic carbo- and heterocyclic scaffolds combining different ring sizes through transannular Morita-Baylis-Hillman reaction catalyzed by a chiral enantiopure bifunctional phosphine. The reaction is remarkably wide in scope and enables the use of a variety of medium and large size ketoenone substrates leading to the final products in high yields and providing excellent stereocontrol in the formation of a quaternary stereogenic center at the ring fusion. Moreover, its potential as a general tool in organic synthesis was highlighted through the accomplishment of the first enantioselective total synthesis of (-)-γ-gurjunene, a sesquiterpene natural product. The experimental process involved the reaction of (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas: 286454-86-2Name: (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine)

(S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas:286454-86-2) is one of aminophosphine type ligands. An increased interest in aminophosphine type ligands used for asymmetric synthesis has been witnessed.Name: (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine This growth in popularity of aminophosphine ligands in asymmetric synthesis is in part due to the growing number of convenient synthetic pathways leading to useful ligand sets.

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

In 2020,Chemical Communications (Cambridge, United Kingdom) included an article by Du, Mengyuan; Yu, Longhui; Du, Ting; Li, Zhaokun; Luo, Yueyang; Meng, Xiangyu; Tian, Zhengtao; Zheng, Changwu; Cao, Weiguo; Zhao, Gang. SDS of cas: 286454-86-2. The article was titled 《N-Protecting group tuning of the enantioselectivity in Strecker reactions of trifluoromethyl ketimines to synthesize quaternary α-trifluoromethyl amino nitriles by ion pair catalysis》. The information in the text is summarized as follows:

An enantioselective Strecker reaction to construct trifluoromethylated quaternary stereocenters with N-PMP and unexplored N-Boc trifluoromethyl ketimines RC(CF3)=NR1 [R = Ph, 3,5-difluorophenyl, thiophen-2-yl, etc.; R1 = 4-methoxyphenyl, C(O)OC(CH3)3] catalyzed using an organophosphine dual-reagent catalyst has been developed. The enantioselectivities of the corresponding products (R/S)-RC(CF3)(CN)NH(R1) with the same catalyst could be switched by using different N-protecting groups (N-PMP or N-Boc). The trifluoromethyl amino nitriles (R/S)-RC(CF3)(CN)NH(R1) were obtained in high yield and high enantioselectivity in a short time and could be easily converted to a variety of useful trifluoromethyl-containing compounds The results came from multiple reactions, including the reaction of (S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas: 286454-86-2SDS of cas: 286454-86-2)

(S)-1-(Diphenylphosphino)-3,3-dimethylbutan-2-amine(cas:286454-86-2) is one of aminophosphine type ligands. An increased interest in aminophosphine type ligands used for asymmetric synthesis has been witnessed.SDS of cas: 286454-86-2 This growth in popularity of aminophosphine ligands in asymmetric synthesis is in part due to the growing number of convenient synthetic pathways leading to useful ligand sets.

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis