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S N 2 Reactions at Tertiary Carbon Centers in Epoxides
Author(s) -
Zhang YongQiang,
Poppel Christina,
Panfilova Anastasia,
Bohle Fabian,
Grimme Stefan,
Gansäuer Andreas
Publication year - 2017
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.201702882
Subject(s) - carbon fibers , chemistry , chemical reaction , diol , quantum chemical , organic chemistry , materials science , molecule , composite material , composite number
Described herein is a novel concept for S N 2 reactions at tertiary carbon centers in epoxides without activation of the leaving group. Quantum chemical calculations show why S N 2 reactions at tertiary carbon centers are proceeding in these systems. The reaction allows flexible synthesis of 1,3‐diol building blocks for natural product synthesis with excellent control of the relative and absolute configurations.