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通过铑催化的芳基硼酸与环状 N-磺酰基亚胺加成反应进行(三芳基)甲基胺的不对称合成。

Asymmetric synthesis of (triaryl)methylamines by rhodium-catalyzed addition of arylboroxines to cyclic N-sulfonyl ketimines.

机构信息

Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.

出版信息

J Am Chem Soc. 2012 Mar 21;134(11):5056-9. doi: 10.1021/ja300697c. Epub 2012 Mar 8.

DOI:10.1021/ja300697c
PMID:22394013
Abstract

Asymmetric addition of arylboroxines to cyclic N-sulfonyl ketimines proceeded in the presence of a rhodium catalyst coordinated with a chiral diene ligand to give high yields of benzosultams, where a triaryl-substituted stereogenic carbon center was created with high enantioselectivity (93-99% ee). The chiral benzosultams were transformed into the chiral (triaryl)methylamines by breaking the cyclic structure.

摘要

在铑催化剂与手性二烯配体配位的存在下,芳基硼酸与环状 N-磺酰基亚胺进行不对称加成,以高产率得到苯并噻唑烷,其中三芳基取代的手性碳原子中心具有高对映选择性(93-99%ee)。通过破坏环状结构,手性苯并噻唑烷可转化为手性(三芳基)甲胺。

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