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Water plays a crucial role: Small molecule catalyzed C–C/C–X bond forming reactions using organosilicon reagents under “wet” conditions
Tetrahedron ( IF 2.1 ) Pub Date : 2020-05-08 , DOI: 10.1016/j.tet.2020.131254
Prithwish Goswami , Jin Hyun Park , Han Yong Bae

Organocatalytic manipulation of silicon reagents, which enables the efficient formation of carbon–carbon (C–C) or carbon–heteroatom (C–X) bonds have been attracting considerable attention since the past few decades. In several instances, surprisingly, water is a remarkably essential molecule to promote the desired transformation to achieve superb outcomes in terms of reaction rates, chemical yields, and stereoselectivities. From the catalytic amount to solvent quantity, water plays a crucial role in the asymmetric/non-asymmetric catalytic transformations such as aldol reactions, Michael addition reactions, Mannich reactions, α-alkylation reactions, and other related strategies. In the current review, we present a comprehensive report on the recent advances of small molecule catalyzed addition reactions of organosilicon reagents under “wet” condition (46 examples). Examples featuring in the synthesis of complex natural products are also discussed.



中文翻译:

水起着至关重要的作用:在“湿”条件下,使用有机硅试剂催化小分子催化的C–C / C–X键形成反应

硅试剂的有机催化操作能够有效地形成碳-碳(CC)或碳-杂原子(C-X)键,这在过去的几十年中引起了广泛的关注。在一些情况下,令人惊讶地,在反应速率,化学收率和立体选择性方面,水是显着必要的分子以促进所需的转化以实现极好的结果。从催化量到溶剂量,水在不对称/不对称催化转化(例如羟醛反应,迈克尔加成反应,曼尼希反应,α-烷基化反应和其他相关策略)中起关键作用。在目前的评论中,我们就“湿”条件下有机硅试剂的小分子催化加成反应的最新进展提供了全面的报告(46个例子)。还讨论了复杂天然产物合成中的实例。

更新日期:2020-05-08
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