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Asymmetric Synthesis of Dihydronaphthalene‐1,4‐Diones via Carbene‐Catalyzed Stereodivergent Reaction
Author(s) -
Zhao Zhifei,
Yang Shuang,
Lan Shouang,
Liu Jinggong,
Liu Shuhua,
Fang Xinqiang
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900506
Subject(s) - chemistry , stereocenter , carbene , benzoin , racemization , enantioselective synthesis , catalysis , aldol reaction , umpolung , combinatorial chemistry , stereochemistry , organic chemistry , nucleophile
2‐Hydroxy‐2,3‐dihydronaphthalene‐1,4‐diones (HDNDs) are ubiquitous in natural products and bioactive molecules, but the rapid asymmetric construction of such scaffolds remains a significant challenge to date. Reported herein is the rapid construction of the above key units via carbene‐catalyzed benzoin reaction. The resolution technique of divergent reaction on racemic mixture (divergent RRM) was employed, affording both isomers of HDNDs in a one‐step fashion. Disubstituted substrates afford products with two contiguous quaternary stereocenters. A series of highly selective transformations on the products can be realized, and mechanistic studies indicate that the benzoin reaction is much faster than the racemization process and the aldol reaction.