An organocatalytic asymmetric sequential allylic alkylation-cyclization of Morita-Baylis-Hillman carbonates and 3-hydroxyoxindoles

An organocatalytic asymmetric sequential allylic alkylation-cyclization of Morita-Baylis-Hillman carbonates and 3-hydroxyoxindoles

The first organocatalytic asymmetric sequential allylic alkylation-cyclization of Morita-Baylis-Hillman carbonates and 3-hydroxyoxindoles has been developed to afford spirooxindoles bearing α-methylene-γ-butyrolactone motifs in 25-85% yield, 60-94% ee and up to >20 : 1 diastereoselectivity.

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2013-10, Vol.49 (82), p.9422-9424
Hauptverfasser: Wang, Qi-Lin, Peng, Lin, Wang, Fei-Ying, Zhang, Ming-Liang, Jia, Li-Na, Tian, Fang, Xu, Xiao-Ying, Wang, Li-Xin
Format: Artikel
Sprache:eng
Schlagworte:
Alkylation
Allyl Compounds - chemistry
Carbonates - chemistry
Catalysis
Cyclization
Indoles - chemistry
Molecular Structure
Spiro Compounds - chemistry
Stereoisomerism
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container_end_page 9424
container_issue 82
container_start_page 9422
container_title Chemical communications (Cambridge, England)
container_volume 49
creator Wang, Qi-Lin
Peng, Lin
Wang, Fei-Ying
Zhang, Ming-Liang
Jia, Li-Na
Tian, Fang
Xu, Xiao-Ying
Wang, Li-Xin
description The first organocatalytic asymmetric sequential allylic alkylation-cyclization of Morita-Baylis-Hillman carbonates and 3-hydroxyoxindoles has been developed to afford spirooxindoles bearing α-methylene-γ-butyrolactone motifs in 25-85% yield, 60-94% ee and up to >20 : 1 diastereoselectivity.
doi_str_mv 10.1039/c3cc45139a
format Article
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source MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Alkylation
Allyl Compounds - chemistry
Carbonates - chemistry
Catalysis
Cyclization
Indoles - chemistry
Molecular Structure
Spiro Compounds - chemistry
Stereoisomerism
title An organocatalytic asymmetric sequential allylic alkylation-cyclization of Morita-Baylis-Hillman carbonates and 3-hydroxyoxindoles
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