Organocatalytic, Asymmetric [2+2+2] Annulation to Construct Six-Membered Spirocyclic Oxindoles with Six Continuous Stereogenic Centers

Lactols and cyclic hemiaminals were directly used in a one-pot organo/organo dual catalytic system induced [2+2+2] tandem reaction for the asymmetric construction of six-membered carbocycles. The enamine-based stereoselective Michael addition of lactols or cyclic hemiaminals to electron-deficient ol...

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Main Authors:	Zhi-Long Li, Chao Liu, Rui Tan, Zhi-Ping Tong, Yan-Kai Liu
Format:	Article
Language:	English
Published:	MDPI AG 2016-04-01
Series:	Catalysts
Subjects:	asymmetric organocatalysis tandem reaction lactol cyclic hemiaminal [2+2+2] annulation spirocyclic oxindole
Online Access:	http://www.mdpi.com/2073-4344/6/5/65

id	doaj-67dbf288bca144d78a21b76d32910b8c
record_format	Article
spelling	doaj-67dbf288bca144d78a21b76d32910b8c2020-11-25T00:07:55ZengMDPI AGCatalysts2073-43442016-04-01656510.3390/catal6050065catal6050065Organocatalytic, Asymmetric [2+2+2] Annulation to Construct Six-Membered Spirocyclic Oxindoles with Six Continuous Stereogenic CentersZhi-Long Li0Chao Liu1Rui Tan2Zhi-Ping Tong3Yan-Kai Liu4School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031, ChinaKey Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaSchool of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031, ChinaSchool of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031, ChinaKey Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaLactols and cyclic hemiaminals were directly used in a one-pot organo/organo dual catalytic system induced [2+2+2] tandem reaction for the asymmetric construction of six-membered carbocycles. The enamine-based stereoselective Michael addition of lactols or cyclic hemiaminals to electron-deficient olefinic oxindole motifs provided chiral C4 components, which were further combined with triethylamine catalyzed Michael/Henry sequential reactions affording spirocyclic oxindole derivatives containing six continuous stereogenic centers with excellent enantioselectivities as a single diastereoisomer. All these desired products have versatile molecular complexity, which might have potential applications in synthetic organic chemistry and the pharmaceutical industry.http://www.mdpi.com/2073-4344/6/5/65asymmetric organocatalysistandem reactionlactolcyclic hemiaminal[2+2+2] annulationspirocyclic oxindole
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Zhi-Long Li Chao Liu Rui Tan Zhi-Ping Tong Yan-Kai Liu
spellingShingle	Zhi-Long Li Chao Liu Rui Tan Zhi-Ping Tong Yan-Kai Liu Organocatalytic, Asymmetric [2+2+2] Annulation to Construct Six-Membered Spirocyclic Oxindoles with Six Continuous Stereogenic Centers Catalysts asymmetric organocatalysis tandem reaction lactol cyclic hemiaminal [2+2+2] annulation spirocyclic oxindole
author_facet	Zhi-Long Li Chao Liu Rui Tan Zhi-Ping Tong Yan-Kai Liu
author_sort	Zhi-Long Li
title	Organocatalytic, Asymmetric [2+2+2] Annulation to Construct Six-Membered Spirocyclic Oxindoles with Six Continuous Stereogenic Centers
title_short	Organocatalytic, Asymmetric [2+2+2] Annulation to Construct Six-Membered Spirocyclic Oxindoles with Six Continuous Stereogenic Centers
title_full	Organocatalytic, Asymmetric [2+2+2] Annulation to Construct Six-Membered Spirocyclic Oxindoles with Six Continuous Stereogenic Centers
title_fullStr	Organocatalytic, Asymmetric [2+2+2] Annulation to Construct Six-Membered Spirocyclic Oxindoles with Six Continuous Stereogenic Centers
title_full_unstemmed	Organocatalytic, Asymmetric [2+2+2] Annulation to Construct Six-Membered Spirocyclic Oxindoles with Six Continuous Stereogenic Centers
title_sort	organocatalytic, asymmetric [2+2+2] annulation to construct six-membered spirocyclic oxindoles with six continuous stereogenic centers
publisher	MDPI AG
series	Catalysts
issn	2073-4344
publishDate	2016-04-01
description	Lactols and cyclic hemiaminals were directly used in a one-pot organo/organo dual catalytic system induced [2+2+2] tandem reaction for the asymmetric construction of six-membered carbocycles. The enamine-based stereoselective Michael addition of lactols or cyclic hemiaminals to electron-deficient olefinic oxindole motifs provided chiral C4 components, which were further combined with triethylamine catalyzed Michael/Henry sequential reactions affording spirocyclic oxindole derivatives containing six continuous stereogenic centers with excellent enantioselectivities as a single diastereoisomer. All these desired products have versatile molecular complexity, which might have potential applications in synthetic organic chemistry and the pharmaceutical industry.
topic	asymmetric organocatalysis tandem reaction lactol cyclic hemiaminal [2+2+2] annulation spirocyclic oxindole
url	http://www.mdpi.com/2073-4344/6/5/65
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Organocatalytic, Asymmetric [2+2+2] Annulation to Construct Six-Membered Spirocyclic Oxindoles with Six Continuous Stereogenic Centers

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