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Catalytic Asymmetric Synthesis of Dihydropyrido[1,2‐ a ]indoles from Nitrones and Allenoates
Author(s) -
Pace Wiktoria H.,
Mo DongLiang,
Reidl Tyler W.,
Wink Donald J.,
Anderson Laura L.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201602568
Subject(s) - squaramide , reagent , chemistry , catalysis , combinatorial chemistry , indole test , transformation (genetics) , scope (computer science) , substituent , allene , enantioselective synthesis , cascade reaction , organocatalysis , organic chemistry , computer science , biochemistry , gene , programming language
Abstract An asymmetric method for the synthesis of dihydropyrido[1,2‐ a ]indoles from mixtures of nitrones and allenoates has been developed. This transformation showcases the use of squaramide catalysis in a complicated cascade system that has been shown to be highly sensitive to reaction conditions and substituent effects. The new method provides access to enantiomerically enriched dihydropyridoindoles from modular, non‐indole reagents. The optimization and scope of the new transformation is discussed in addition to initial mechanistic experiments that indicate the role of the catalyst.