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Reductive Amination/Cyclization of Keto Acids Using a Hydrosilane for Selective Production of Lactams versus Cyclic Amines by Switching of the Indium Catalyst
Author(s) -
Ogiwara Yohei,
Uchiyama Takuya,
Sakai Norio
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201509465
Subject(s) - reductive amination , silane , catalysis , indium , chemistry , amination , combinatorial chemistry , reducing agent , lactam , selective catalytic reduction , organic chemistry
Described herein is that the catalytic construction of N‐substituted five‐ and six‐membered lactams from keto acids with primary amines by reductive amination, using an indium/silane combination. This relatively benign and safe catalyst/reductant system tolerates the use of a variety of functional groups, especially ones that are reduction‐sensitive. A direct switch from synthesizing lactams to synthesizing cyclic amines is achieved by changing the catalyst from In(OAc) 3 to InI 3 . This conversion occurs by further reduction of the lactam using the indium/silane pair.