Resolution of 2,2-Disubstituted Epoxides via Biocatalytic Azidolysis

被引：55
作者：
Molinaro, Carmela [1 ]
Guilbault, Audrey-Anne [1 ]
Kosjek, Birgit [2 ]
机构：
[1] Merck Frosst Ctr Therapeut Res, Dept Proc Res, Kirkland, PQ H9H 3L1, Canada
[2] Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 17期
关键词：
ASYMMETRIC ALKENE AZIRIDINATION; HALOHYDRIN DEHALOGENASE; ENANTIOSELECTIVE AZIRIDINATION; DIMETHYLSULFONIUM METHYLIDE; 1,2-AMINO ALCOHOLS; HYDROGENATION; DERIVATIVES; CONVERSION; COMPLEXES; CATALYSTS;
D O I：
10.1021/ol101406k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A practical procedure for the enzymatic resolution of 2-alkyl-2-aryl-disubstituted epoxides using the Codex HHDH P2E2 enzyme and sodium azide is reported. This method allowed the synthesis of novel regio- and enantioselective 1-azido-2-arylpropan-2-ols in excellent yields. Furthermore, these intermediates were used for the preparation of enantiomerically enriched amino alcohols and aziridines containing a tertiary center.
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收藏
页码：3772 / 3775
页数：4
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