Premium
1,6‐Conjugate Addition of 1,3‐Dicarbonyl Compounds to para ‐Quinone Methides Enabled by Noncovalent N‐Heterocyclic Carbene Catalysis
Author(s) -
Santra Surojit,
Porey Arka,
Guin Joyram
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700656
Subject(s) - chemistry , catalysis , carbene , conjugate , enantioselective synthesis , organocatalysis , combinatorial chemistry , substrate (aquarium) , quinone , non covalent interactions , organometallic chemistry , organic chemistry , molecule , mathematical analysis , hydrogen bond , oceanography , mathematics , geology
Catalysis with N‐heterocyclic carbenes (NHCs) via substrate activation through noncovalent interactions offers a great opportunity to perform organic transformations. Herein, we demonstrate an efficient catalytic method for the 1,6‐conjugate addition of 1,3‐dicarbonyl compounds to para ‐quinone methides ( p ‐QMs) using NHCs as Brønsted‐base catalysts. The method is applicable to a wide range of functionalized substrates with respect to both 1,3‐diketones and p ‐QMs. An initial study using chiral NHCs provides information on the feasibility of developing a catalytic enantioselective variant of this reaction.