Asymmetric Desymmetrization of 1,3-Diketones via Intramolecular Benzoin Reaction

A general method for the asymmetric desymmetrization of 1,3-diketone substrates via chiral N-heterocyclic carbene catalyzed intramolecular benzoin reactions was developed. Five- and six-membered cyclic ketones bearing two contiguous fully substituted stereocenters were generated with excellent diast...

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Published inJournal of organic chemistry Vol. 81; no. 7; pp. 2763 - 2769
Main Authors Li, Yuanzhen, Yang, Shuang, Wen, Genfa, Lin, Qiqiao, Zhang, Guoxiang, Qiu, Lin, Zhang, Xiaoyan, Du, Guangfen, Fang, Xinqiang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.04.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
N-HETEROCYCLIC CARBENE
ENANTIOSELECTIVE SYNTHESIS
PHOTOISOMERIZATION
CATALYZED-REACTIONS
CONSTRUCTION
QUATERNARY STEREOCENTERS
HYDROBENZOFURANONES
ORGANOCATALYSIS
STETTER REACTION
CYCLOHEXADIENONES
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Summary:A general method for the asymmetric desymmetrization of 1,3-diketone substrates via chiral N-heterocyclic carbene catalyzed intramolecular benzoin reactions was developed. Five- and six-membered cyclic ketones bearing two contiguous fully substituted stereocenters were generated with excellent diastereoselectivities and moderate to excellent enantioselectivities.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b02829