OPTICALLY-ACTIVE BUILDING-BLOCKS FROM THE SPAC REACTION - A COMPLETELY ASYMMETRIC-SYNTHESIS OF (4S-CIS)-5-(CYCLOHEXYLMETHYL)-4-HYDROXY-2-PYRROLIDINONE, A STATINE ANALOG
OPTICALLY-ACTIVE BUILDING-BLOCKS FROM THE SPAC REACTION - A COMPLETELY ASYMMETRIC-SYNTHESIS OF (4S-CIS)-5-(CYCLOHEXYLMETHYL)-4-HYDROXY-2-PYRROLIDINONE, A STATINE ANALOG
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DOI：
10.1021/jo00006a017
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发表时间：
1991-03-15
影响因子：
3.6
通讯作者：
HENDERSON, I
中科院分区：
文献类型：
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作者：
BURGESS, K;CASSIDY, J;HENDERSON, I
定义了控制光学活性亚磺酰乙酸酯 2 与醛反应（“SPAC”反应）中形成的甲基 γ-羟基-α,β-不饱和酯 1 的化学和光学产率的因素。这些chirons (1) 的外消旋样品可以通过脂肪酶假单胞菌K-10 在有机溶剂中的粗制剂介导的酰化作用来解析。不对称 SPAC 反应与这些生物催化拆分的组合提供了以良好产率获得高光学活性酯 1 的途径。该方法应用于 (4S-顺式)-5-(环己基甲基)-4-羟基-2-吡咯烷酮 (15) 的完全不对称合成，(15) 是 (3S,4S)-4-氨基-5-环己基-3-羟基戊酸 (ACHPA) 的环状衍生物。
Factors that govern chemical and optical yields of methyl gamma-hydroxy-alpha,beta-unsaturated esters 1 formed in reactions of optically active sulfinylacetates 2 with aldehydes (the ''SPAC'' reaction) are defined. Racemic samples of these chirons (1) can be resolved via acylations mediated by crude preparations of the lipase Pseudomonas K-10 in organic solvents. Combinations of asymmetric SPAC reactions with these biocatalytic resolutions provide routes to highly optically active esters 1 in good yields. This methodology is applied in a completely asymmetric synthesis of (4S-cis)-5-(cyclohexylmethyl)-4-hydroxy-2-pyrrolidinone (15), a cyclic derivative of (3S,4S)-4-amino-5-cyclohexyl-3-hydroxypentanoic acid (ACHPA).