Dual catalyst control in the enantioselective intramolecular Morita-Baylis-Hillman reaction

被引：110

作者：

Aroyan, CE ^{[1
]}

Vasbinder, MM ^{[1
]}

Miller, SJ ^{[1
]}

机构：

[1] Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 18期

关键词：

D O I：

10.1021/ol0513544

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The intramolecular Morita-Baylis-Hillman (MBH) reaction has been achieved with unprecedented levels of enantioselectivity. Using a cocatalyst system involving pipecolinic acid and N-methylimidazole, cyclic MBH products have been obtained with enantiomer ratios of 92:8 (84% ee). In addition, reactions may be carried out with a "kinetic resolution quench" involving acetic anhydride and an asymmetric acylation catalyst such that ee enhancement occurs to deliver products with > 98% ee with an isolated yield of 50%.

引用

页码：3849 / 3851

页数：3

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