Catalytic Asymmetric Synthesis of γ-Substituted Vinyl Sulfones
Catalytic Asymmetric Synthesis of γ-Substituted Vinyl Sulfones
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DOI：
10.1002/chem.201003177
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发表时间：
2011-02-01
影响因子：
4.3
通讯作者：
Palomo, Claudio
中科院分区：
文献类型：
--
作者：
Lopez, Rosa;Zalacain, Maitane;Palomo, Claudio
为伽马取代乙烯基砜的立体选择性构筑提供了一种快速的新途径。成功的关键是使用容易获得的手性仲胺催化剂，这种催化剂允许在共轭加成中使用碱敏感的β-硝基乙基砜作为掩蔽的β-磺酰基乙烯基阴离子。该方法在三步一锅操作中进行，以良好的产率和良好的对映选择性获得了多种乙烯基砜。该方法也已扩展到其他相对碱敏感的β-电子吸收取代的硝基烷烃，以提供具有多种功能的产品，为有机合成提供了一条快速进入非常有吸引力的合成中间体的途径。
A fast new entry for the stereoselective construction of gamma-substituted vinyl sulfones is presented. The key for success is the use of a readily available chiral secondary amine catalyst that allows the use of base-sensitive beta-nitroethyl sulfones as masked beta-sulfonyl vinyl anions in conjugate additions. The method performed in a three-step one-pot operation gives access to a great variety of vinyl sulfones in good yields and with excellent enantioselectivities. The method has also been extended to other relatively base-sensitive beta-electron-withdrawing-substituted nitroalkanes to afford products with manifold functionality, providing a quick entry to very attractive synthetic intermediates for organic synthesis.