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Enantioselective N‐Heterocyclic Carbene Catalyzed Cyclopentene Synthesis via the β‐Azolium Ylide
Author(s) -
Scott Lydia,
Nakano Yuji,
Zhang Changhe,
Lupton David W.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201804271
Subject(s) - ylide , carbene , enantioselective synthesis , cycloisomerization , chemistry , catalysis , cyclopentene , organocatalysis , kinetic resolution , combinatorial chemistry , stereochemistry , organic chemistry
Herein we report the cycloisomerization of electron‐poor 1,5‐dienes via the β‐azolium ylide to give enantioenriched cyclopentenes. The reaction is mediated by a chiral N‐heterocyclic carbene (NHC) catalyst, exploits readily available substrates, has good generality (17 examples), and displays excellent enantioselectivity (mostly >94:6). Studies demonstrating the viability of a related dynamic kinetic resolution are reported, as are those with alternate tethers and derivatizations.