Highly enantioselective [4+2]cycloaddition reactions catalyzed by a chiral N-methyl-oxazaborolidinium cation
Highly enantioselective [4+2]cycloaddition reactions catalyzed by a chiral N-methyl-oxazaborolidinium cation
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DOI：
10.1021/ol8011502
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发表时间：
2008-08-07
期刊：
影响因子：
5.2
通讯作者：
Corey, E. J.
中科院分区：
文献类型：
--
作者：
Canales, Eda;Corey, E. J.
芳基硼氢化锂与β-氨基醇盐的反应为恶唑硼烷的合成提供了一条新的途径。该方法还导致迄今难以实现的N-甲基恶唑硼烷阳离子的首次合成，特别是阳离子脯氨酸衍生物3。化合物3是一种强手性刘易斯酸，它对催化[4 + 2]-环加成反应非常有效，产率高，对映选择性高。几个不同的例子说明了这些催化反应的范围。
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.