N‐Heterocyclic Carbene‐Catalyzed Intramolecular Nucleophilic Substitution: Enantioselective Construction of All‐Carbon Quaternary Stereocenters | Zendy

Zhao Ming | Zendy; Chen Jie | Zendy; Yang Hui | Zendy; Zhou Ling | Zendy

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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.

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