Asymmetric synthesis of cyclic indole aminals via 1,3-stereoinduction.

J Org Chem

Department of Process Chemistry, Merck Research Laboratories, Merck & Co., Inc. , Rahway, New Jersey 07065, United States.

Published: September 2014

A general and efficient asymmetric synthesis of cyclic indoline aminals was developed with a high level of 1,3-stereoinduction through a dynamic crystallization-driven condensation. Dehydrogenation of the indoline aminals with potassium permanganate produced the corresponding cyclic indole aminals in high yields and excellent enantioselectivities. This general methodology was successfully applied to the synthesis of a wide variety of chiral cyclic indoline aminals and indole aminals with aromatic and aliphatic functional groups.

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http://dx.doi.org/10.1021/jo501581eDOI Listing

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