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Combining Organocatalysis and Photoredox Catalysis: An Asymmetric Synthesis of Chiral β‐ Amino α‐ Substituted Tryptamines
Author(s) -
Levitre Guillaume,
Audubert Clément,
Dumoulin Audrey,
Goual Nawel,
Retailleau Pascal,
Moreau Xavier,
Masson Géraldine
Publication year - 2019
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201901266
Subject(s) - tryptamines , chemistry , organocatalysis , enantioselective synthesis , electrophilic amination , amination , stereoselectivity , catalysis , electrophile , organic chemistry , combinatorial chemistry , stereochemistry , tryptamine , biochemistry
A stereoselective synthesis of functionalized β‐ amino α‐ substituted tryptamines has been achieved by a sequential asymmetric organocatalytic three‐component electrophilic amination and photocatalyzed Friedel‐Crafts reaction of indoles with moderate to high diastereoselectivities (up to >99 : 1 dr) and excellent enantioselectivities (up to >99 % ee ). We also demonstrated that the β ‐amino α ‐substituted tryptamines can be successfully engaged in a further catalytic step, furnishing various α , β ‐substituted tryptamines without erosion of enantioselectivity and with complete diastereoselectivity.