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Enantioselective Organocatalytic Fluorination‐Induced Wagner–Meerwein Rearrangement
Author(s) -
RomanovMichailidis Fedor,
Guénée Laure,
Alexakis Alexandre
Publication year - 2013
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.201303527
Subject(s) - enantioselective synthesis , scope (computer science) , substrate (aquarium) , chemistry , allylic rearrangement , ring (chemistry) , strain (injury) , stereochemistry , catalysis , computer science , combinatorial chemistry , biology , organic chemistry , ecology , anatomy , programming language
Cracked under strain : Strained allylic cyclobutanols and cyclopropanols readily undergo a ring expansion described by the title rearrangement. This reaction is promoted by catalytic amounts of 1 and displays high tolerance with respect to the substrate scope. The corresponding β‐fluoro spiroketone products are isolated in high yields and with excellent stereoselectivities. EDG=electron‐donating group, EWG=electron‐withdrawing group.
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