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1,3‐Allylic Strain as a Strategic Diversification Element for Constructing Libraries of Substituted 2‐Arylpiperidines
Author(s) -
Coombs Thomas C.,
Lushington Gerald H.,
Douglas Justin,
Aubé Jeffrey
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201007133
Subject(s) - leverage (statistics) , diversification (marketing strategy) , element (criminal law) , strain (injury) , computer science , stereochemistry , information retrieval , biology , chemistry , political science , artificial intelligence , business , law , marketing , anatomy
Flipping diversity : Minimization of 1,3‐allylic strain (A 1, 3 strain) is a recurring element in the design of a stereochemically and spatially diverse collection of 2‐arylpiperidines. A 1, 3 strain guides the regioselective addition of nucleophiles and N‐substituents leverage A 1, 3 strain to direct each stereoisomer to two different conformer populations, thus doubling the number of library members.