Recommanded Product: 40400-13-3. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 1-(Bromomethyl)-2-iodobenzene, is researched, Molecular C7H6BrI, CAS is 40400-13-3, about Enantioselective Rh(II)-Catalyzed Desymmetric Cycloisomerization of Diynes: Constructing Furan-Fused Dihydropiperidines with an Alkyne-Substituted Aza-Quaternary Stereocenter. Author is Wu, Rui; Lu, Jiajun; Cao, Tongxiang; Ma, Jun; Chen, Kai; Zhu, Shifa.
Herein, an enantioselective dirhodium(II)-catalyzed cycloisomerization of diynes R1CCC(R2)(R3)XCH2CCHO (R1 = H, t-Bu, 4-fluorophenyl, tri-Me silyl, etc.; R2 = t-Bu, Ph, 4-cyanophenyl, etc.; R3 = cyclopropyl, Ph, propan-2-yl, etc.; X = NTs, O, C) is achieved by the strategy of desymmetrization, which not only represents a new cycloisomerization reaction of diynes but also constitutes the first Rh(II)-catalyzed asym. intramol. cycloisomerization of 1,6-diynes. This protocol provides a range of valuable furan-fused dihydropiperidine derivatives I with an enantiomerically enriched alkynyl-substituted aza-quaternary stereocenter in high efficiency, complete atom economy, and excellent enantioselectivity (up to 98% ee). Besides, the highly functionalized products could be easily transformed into various synthetically useful building blocks and conjugated with a series of pharmaceutical mols. The mechanism involving a concerted [3+2] cycloaddition/[1,2]-H shift of the Rh(II) carbenoid intermediate was elucidated by DFT calculations and mechanistic studies. More importantly, the first single crystal of alkyne-dirhodium(II) was obtained to show that a η2-coordinating activation of alkynal by dirhodium(II) was involved. Weak hydrogen bondings between the carboxylate ligands and alkynal were found, which probably made the well-defined paddlewheel-like dirhodium(II) distinctive from other metal complexes in catalyzing this transformation. Furthermore, the origin of the enantioselectivity was elucidated by a Rh2(R-PTAD)4-alkyne complex and addnl. calculational studies.
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Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate