Stereoselective and enantioselective synthesis of anti-1-(Trifluoromethyl) amino alcohols

被引:20
作者
Abouabdellah, A [1 ]
Bègué, JP [1 ]
Bonnet-Delpon, D [1 ]
Kornilov, A [1 ]
Rodrigues, I [1 ]
Richard, C [1 ]
机构
[1] BIOCIS, URA CNRS 1843, Fac Pharm, F-92296 Chatenay Malabry, France
关键词
D O I
10.1021/jo9805448
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
anti-(Trifluoromethyl) beta-amino alcohols 2 have been prepared in good yields and with 90% diastereoisomeric excess through a reaction of 1-(trifluoromethyl) epoxy ethers 3 with dimethylaluminum amide, followed by the in situ chelation-controlled stereoselective reduction of the intermediate amino ketone. The salen-mediated chiral epoxidation of 1-(trifluoromethyl) enol ether 4a led to the homochiral epoxy ethers 11a and 12a in a good enantiomeric excess. Reaction with dimethylaluminum amide followed by a reduction step provided the chiral amino alcohols 15a and 16a, respectively.
引用
收藏
页码:6529 / 6534
页数:6
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