CHIRAL SYNTHESIS VIA ORGANOBORANES .39. A FACILE SYNTHESIS OF GAMMA-SUBSTITUTED-GAMMA-BUTYROLACTONES IN EXCEPTIONALLY HIGH ENANTIOMERIC PURITY

被引：115
作者：
BROWN, HC
KULKARNI, SV
RACHERLA, US
机构：
[1] H. C. Brown and R. B. Wetherill Laboratories of Chemistry, Purdue University, West Lafayette, Indiana 47907
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 02期
关键词：
D O I：
10.1021/jo00081a014
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Optically active homoallylic alcohols of exceptionally high enantiomeric purity (98-greater than or equal to 99 % ee) readily available via asymmetric allylboration were converted into p-nitrobenzoate esters and subjected to hydroboration followed by oxidation with CrO3 in aqueous acetic acid (10% H2O) to obtain the corresponding carboxylic acids with the same number of carbon atoms. The protecting ester group was hydrolyzed and the product lactonized in situ to the gamma-substituted gamma-butyrolactones 5 (R = Me, Pr, i-Pr, t-Bu, Ph, (E)-CH=CHCH3) usually without racemization and in good yields. The method is convenient and potentially valuable for. the synthesis of highly functionalized gamma-butyrolactones in high optical purity.
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页码：365 / 369
页数：5
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