Enantioselective addition of diethylzinc to aldehydes catalyzed by 5-cis-substituted proline derivatives
Enantioselective addition of diethylzinc to aldehydes catalyzed by 5-cis-substituted proline derivatives
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DOI：
10.1016/j.tet.2018.11.030
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发表时间：
2019-01-03
期刊：
影响因子：
2.1
通讯作者：
Breuning, Matthias
中科院分区：
文献类型：
--
作者：
Prause, Felix;Wagner, Stefan;Breuning, Matthias
5- o -取代脯氨酸醇、脯氨酸胺和脯氨酸胺磺胺被证明是二乙基锌对醛的对映选择性加成的有效配体，提供高达99%的ee。不对称诱导感可由外环官能团（CPh2OH vs. CH2NHR vs. CH2NHSO3R）的性质控制。额外的5-顺式取代基对手性转移有很强的有利影响，因为它使催化剂结构刚性。在各自的过渡态上详细讨论了反应的立体化学结果。(C) 2018 Elsevier Ltd.版权所有。
5-Os-substituted prolinols, prolinamines, and prolinamine sulfonamides proved to be efficient ligands for the enantioselective addition of diethylzinc to aldehydes, providing up to 99% ee. The sense of asymmetric induction can be controlled by the nature of the exocyclic functional group (CPh2OH vs. CH2NHR vs. CH2NHSO3R). The additional 5-cis substituent exerts a strong beneficial effect on the chirality transfer since it rigidifies the catalyst structure. The stereochemical outcome of the reactions is discussed in detail on the respective transition states. (C) 2018 Elsevier Ltd. All rights reserved.