A CONCISE AND ENANTIOSELECTIVE APPROACH TO CYCLOBUTANONES BY TANDEM ASYMMETRIC EPOXIDATION AND ENANTIOSPECIFIC RING EXPANSION OF CYCLOPROPYLIDENE ALCOHOLS - AN ENANTIOCONTROLLED SYNTHESIS OF (+)-ALPHA-CUPARENONE AND (-)-ALPHA-CUPARENONE

被引：92

作者：

NEMOTO, H ^{[1
]}

ISHIBASHI, H ^{[1
]}

NAGAMOCHI, M ^{[1
]}

FUKUMOTO, K ^{[1
]}

机构：

[1] TOHOKU UNIV,INST PHARMACEUT,SENDAI,MIYAGI 980,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 06期

关键词：

D O I：

10.1021/jo00032a021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A tandem Katsuki-Sharpless asymmetric epoxidation and enantiospecific ring expansion of 2-alkyl(or 2-aryl)-2-cyclopropylideneethanols (1a-i) afforded chiral 1-alkyl(or 1-aryl)-1-(hydroxymethyl)cyclobutanones (3a-i) in high yields and high enantiomeric excess. These compounds are potentially valuable synthons for the enantioselective creation of the quaternary carbons. Hence, this enabled us to accomplish a concise and enantioselective total synthesis of both (+)- and (-)-alpha-cuparenones (11).

引用

页码：1707 / 1712

页数：6

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[1] RECENT ADVANCES IN ASYMMETRIC-SYNTHESIS .2. [J].