1,6‐Conjugate Addition of 1,3‐Dicarbonyl Compounds to  para ‐Quinone Methides Enabled by Noncovalent N‐Heterocyclic Carbene Catalysis | Zendy

Santra Surojit | Zendy; Porey Arka | Zendy; Guin Joyram | Zendy

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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.

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