Yen, Andy; Choo, Ken-Loon; Yazdi, Shabnam K.; Franke, Patrick T.; Webster, Robert; Franzoni, Ivan; Loh, Charles C. J.; Poblador-Bahamonde, Amalia I.; Lautens, Mark published the artcile< Rhodium-Catalyzed Enantioselective Isomerization of meso-Oxabenzonorbornadienes to 1,2-Naphthalene Oxides>, Application In Synthesis of 277306-29-3, the main research area is epoxynaphthalene enantioselective preparation; methoxy hydronaphthalenol enantioselective preparation; rhodium phenylphosphinoferrocenylethylphosphine catalyst enantioselective isomerization oxabicycloheptenedimethanol ester benzyl ether; enantioselective isomerization ring opening oxabicycloheptene methanol rhodium phenylphosphinoferrocenylethylphosphine catalyst; mechanism stereoselectivity isomerization ring opening oxabicycloheptene rhodium phenylphosphinoferrocenylethylphosphine catalyst; acetoxymethyl bromobenzyloxymethyl epoxynaphthalene mol crystal structure; allylic compounds; asymmetric catalysis; enantioselectivity; isomerization; rhodium.
In the presence of Rh(cod)2BF4 and nonracemic diphenylphosphinoferrocenylethylphosphines, oxabicycloheptenedimethanol esters and dibenzyl ethers such as I underwent enantioselective isomerization to yield nonracemic 1,2-epoxynaphthalenes such as II in 53-99% yields and in 95->99% ee. In the presence of Rh(cod)2BF4 and a nonracemic diphenylphosphinoferrocenylethylphosphine, I and II underwent ring opening or tandem isomerization and ring opening reactions to yield methoxydihydronaphthalenols such as III. DFT calculations were performed to account for the stereoselectivities of the isomerization and ring opening reactions; ring-opening reactions of bridgehead disubstituted oxabicyclic alkenes proceed through the intermediacy of 1,2-epoxynaphthalenes and may indicate a kinetically and thermodynamically favored reductive elimination as the origin for the observed enantioselectivities. The structures of II and of a bis(bromobenzyloxymethyl) 1,2-epoxynaphthalene were determined by X-ray crystallog.
Angewandte Chemie, International Edition published new progress about Aralkyl alcohols Role: SPN (Synthetic Preparation), PREP (Preparation). 277306-29-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C32H40FeP2, Application In Synthesis of 277306-29-3.
Referemce:
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