Optimization of the catalytic asymmetric addition of nitroalkanes to cyclic enones with trans-4,5-methano-L-proline

被引：69

作者：

Hanessian, Stephen ^{[1
]}

Shao, Zhihui ^{[1
]}

Warrier, Jayakumar S. ^{[1
]}

机构：

[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 21期

关键词：

D O I：

10.1021/ol0618407

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The conjugate addition of symmetrical 2-nitroalkanes to 2-cycloalkenones catalyzed by trans-4,5-methano-L-proline proceeds with > 99% ee and excellent chemical yields. 1-Nitroalkanes afford diastereomeric syn/anti products that can be separated with good individual enantioselectivities. Proline hydroxamic acid and its trans-4,5-methano-L-proline hydroxamic acid are also effective organocatalysts in the addition of 2-nitropropane to 2-cyclohexenone (75% and 81% ee, respectively).

引用

页码：4787 / 4790

页数：4

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