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N‐Heterocyclic Carbene‐Catalyzed Intramolecular Nucleophilic Substitution: Enantioselective Construction of All‐Carbon Quaternary Stereocenters
Author(s) -
Zhao Ming,
Chen Jie,
Yang Hui,
Zhou Ling
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201700198
Subject(s) - stereocenter , enantioselective synthesis , carbene , intramolecular force , nucleophile , allylic rearrangement , chemistry , nucleophilic substitution , yield (engineering) , stereochemistry , catalysis , medicinal chemistry , combinatorial chemistry , organic chemistry , materials science , metallurgy
An efficient enantioselective N‐heterocyclic carbene (NHC)‐catalyzed intramolecular S N 2′ nucleophilic substitution of aldehydes with ( E / Z )‐trisubstituted allylic bromides was accomplished. A range of enantioenriched chromanones bearing an all‐carbon quaternary stereocenter at the C3 position were prepared with up to 97 % yield and 98 % enantiomeric excess. The resulting vinyl and carbonyl groups in these products can be transformed into a variety of synthetically important building blocks.