Stereoselective synthesis of 1,2-disubstituted β-amino alcohols by nucleophilic addition to N-tert-butanesulfinyl α-alkoxyaldimines

被引:69
作者
Evans, JW [1 ]
Ellman, JA [1 ]
机构
[1] Univ Calif Berkeley, Dept Chem, Ctr New Direct Organ Synth, Berkeley, CA 94720 USA
关键词
D O I
10.1021/jo035224p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-tert-Butanesulfinyl alpha-alkoxyaldimines are readily prepared from protected (S)-lactals without epimerization at the alpha-stereocenter. Addition of ethyl and phenyl Grignard reagents, as well as the titanium enolate of methyl acetate, to the N-tert-butanesulfinyl aldimines provides 1,2-disubstituted beta-amino alcohols in good yields (73-98%) and with high diastereoselectivities. Either syn- or anti-amino alcohol products can be obtained by the appropriate choice of alcohol protecting groups and/or reaction conditions. Finally, deprotection of the addition products provides straightforward access to either syn- or anti-1,2-amino alcohols.
引用
收藏
页码:9948 / 9957
页数:10
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