Asymmetric Cycloadditions of o-Quinone Methides Employing Chiral Ammonium Fluoride Precatalysts

被引：169
作者：
Alden-Danforth, Ethan [1 ]
Scerba, Michael T. [1 ]
Lectka, Thomas [1 ]
机构：
[1] Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA
来源：
ORGANIC LETTERS | 2008年 / 10卷 / 21期
关键词：
D O I：
10.1021/ol802029e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The catalytic, enantioselective, [4 + 2] cycloaddition reaction of ortho-quinone methides with silyl ketene acetals is described. This mechanistically interesting reaction, initiated by a chiral cinchona alkaloid-derived ammonium fluoride "precatalyst" complex, affords a variety of alkyl- and aryl-substituted 3,4-dihydrocoumarin products in excellent yield and with good enantioselectivity.
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页码：4951 / 4953
页数：3
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