Diastereoselective [4+2] reactions of o-quinone methides with a chiral enol ether:: Asymmetric synthesis of (+)-R-mimosifoliol

被引：21

作者：

Selenski, C ^{[1
]}

Mejorado, LH ^{[1
]}

Pettus, TRR ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Biochem & Chem, Santa Barbara, CA 93106 USA

来源：

SYNLETT | 2004年 / 06期

关键词：

benzylic stereocenter; o-quinone methide; Diels-Alder; asymmetric [4+2] cycloaddition; inverse demand; chiral enol ethers; lactol; chroman; benzopyran; total synthesis;

D O I：

10.1055/s-2004-822888

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first examples of enantioselective [4+2] cycloadditions of o-quirione methides (o-QMs) are reported. Their cycloaddition with trans-2-phenyl-1-cyclohexinol derived vinyl ether produces chiral benzopyrans. This procedure offers access to chiral aliphatic benzylic carbons and is applied to the synthesis of (+)-R-mimosifoliol.

引用

页码：1101 / 1103

页数：3

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