Highly enantioselective [4+2]cycloaddition reactions catalyzed by a chiral N-methyl-oxazaborolidinium cation

被引：49

作者：

Canales, Eda ^{[1
]}

Corey, E. J. ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 15期

关键词：

D O I：

10.1021/ol8011502

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of lithium aryl borohydrides with salts of beta-amino alcohols provides a new route for the synthesis of oxazaborolidines. This method also leads to the first synthesis of hitherto elusive N-methyl oxazaborolidine cations, specifically the cationic proline derivative 3. Compound 3 is a strong chiral Lewis acid which is very effective for catalysis of [4 + 2]-cycloaddition reactions in good yield and with high enantioselectivity. Several diverse examples illustrate the scope of these catalytic reactions.

引用

页码：3271 / 3273

页数：3

共 17 条

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