Lewis base-catalyzed asymmetric sulfenylation of alkenes: construction of sulfenylated lactones and application to the formal syntheses of (−)-nicotlactone B and (−)-galbacin

An efficient method for the preparation of chiral sulfenylated lactones has been described based on Lewis base-catalyzed enantioselective sulfenylation of unsaturated carboxylic acids. The scope of this method includes two enantioselective cyclization reactions: 5- endo and 6- exo thiolactonizations...

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Veröffentlicht in:	Chemical communications (Cambridge, England) England), 2019-08, Vol.55 (63), p.9367-937
Hauptverfasser:	Luo, Hui-Yun, Xie, Yu-Yang, Song, Xu-Feng, Dong, Jia-Wei, Zhu, Deng, Chen, Zhi-Min
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkenes Carboxylic acids Chemical reactions Crystallography Enantiomers Lactones Lewis base Natural products
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container_title	Chemical communications (Cambridge, England)
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creator	Luo, Hui-Yun Xie, Yu-Yang Song, Xu-Feng Dong, Jia-Wei Zhu, Deng Chen, Zhi-Min
description	An efficient method for the preparation of chiral sulfenylated lactones has been described based on Lewis base-catalyzed enantioselective sulfenylation of unsaturated carboxylic acids. The scope of this method includes two enantioselective cyclization reactions: 5- endo and 6- exo thiolactonizations of alkenes. Two types of lactones were obtained with up to 95% ee and 99% yield. Additionally, this methodology has been applied in the formal syntheses of bioactive natural products (−)-nicotlactone B and (−)-galbacin. An efficient method for the preparation of chiral sulfenylated lactones was described based on Lewis base-catalyzed enantioselective sulfenylation of alkenes.
doi_str_mv	10.1039/c9cc04758a
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source	Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects	Alkenes Carboxylic acids Chemical reactions Crystallography Enantiomers Lactones Lewis base Natural products
title	Lewis base-catalyzed asymmetric sulfenylation of alkenes: construction of sulfenylated lactones and application to the formal syntheses of (−)-nicotlactone B and (−)-galbacin
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