Enantioselective [4+2] cycloadditions of ο-quinone methides:: Total synthesis of (+)-mimosifoliol and formal synthesis of (+)-tolterodine

被引：85
作者：
Selenski, C [1 ]
Pettus, TRR [1 ]
机构：
[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 26期
关键词：
D O I：
10.1021/jo048703c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first example of an enantioselective cycloaddition of an o-quinone methide (o-QM) with a chiral enol ether is described along with the total synthesis of (+)-mimosifoliol and the formal synthesis of (+)-tolterodine. These syntheses exemplify a three-component, one-pot benzopyran approach for the construction of chiral benzylic junctions. Cycloadditions of various enol ethers and o-QMs are examined, and diastereoselectivities >95% are obtained with trans-2-phenyl-1-cyclohexanol and 2,2-diphenylcyclopentanol vinyl ethers.
引用
收藏
页码：9196 / 9203
页数：8
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