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Highly Enantioselective Lewis Base Organocatalyzed Hydrosilylation of γ‐Imino Esters
Author(s) -
Xue ZhouYang,
Liu LiXin,
Jiang Yan,
Yuan WeiCheng,
Zhang XiaoMei
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101268
Subject(s) - enantioselective synthesis , hydrosilylation , chemistry , trichlorosilane , lewis acids and bases , substrate (aquarium) , organic chemistry , organocatalysis , optically active , base (topology) , amino esters , stereochemistry , catalysis , mathematical analysis , oceanography , mathematics , silicon , geology
Highly enantioselective hydrosilylation of γ‐imino esters with trichlorosilane promoted by a chiral Lewis base proceeded smoothly to provide various optically active γ‐amino esters in good yields (up to 96 %) with excellent enantioselectivities (up to 99 % ee ) at –10 °C in Cl 2 CHCHCl 2 . The side reactions were successfully reduced by rational modification of the substrate. The absolute configuration of one of the γ‐amino esters was determined. Finally, two pharmaceutically interesting enantioenriched γ‐lactams were synthesized from two γ‐amino esters.