Enantioselective Michael/Mannich Polycyclization Cascade of Indolyl Enones Catalyzed by Quinine-Derived Primary Amines

Three′s a crowd: The title reaction provides a tetracylic core bearing three chiral centers (see scheme; Ts=4‐toluenesulfonyl) with excellent enantioselectivity and good diastereoselectivity. The reaction was used to efficiently construct the (+)‐kreysiginine skeleton.

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Bibliographic Details
Published inAngewandte Chemie (International ed.) Vol. 50; no. 37; pp. 8665 - 8669
Main Authors Cai, Quan, Zheng, Chao, Zhang, Jun-Wei, You, Shu-Li
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 05.09.2011
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
amines
Amines - chemistry
asymmetric catalysis
cascade reactions
Catalysis
Chemistry
Chemistry, Multidisciplinary
Cyclization
indoles
Ketones - chemical synthesis
Ketones - chemistry
Molecular Structure
organocatalysis
Physical Sciences
Quinine - chemistry
Science & Technology
Stereoisomerism
IMINIUM ACTIVATION
SIMPLE ALPHA,BETA-UNSATURATED KETONES
amines
MULTISUBSTITUTED CYCLOPENTANES
QUATERNARY STEREOCENTERS
asymmetric catalysis
MICHAEL ADDITION
cascade reactions
organocatalysis
indoles
DIELS-ALDER REACTION
ORGANOCATALYTIC CONJUGATE ADDITION
ASYMMETRIC EPOXIDATION
FRIEDEL-CRAFTS ALKYLATION
ALPHA-BRANCHED ENALS
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Summary:Three′s a crowd: The title reaction provides a tetracylic core bearing three chiral centers (see scheme; Ts=4‐toluenesulfonyl) with excellent enantioselectivity and good diastereoselectivity. The reaction was used to efficiently construct the (+)‐kreysiginine skeleton.
Bibliography:Chinese Academy of Sciences
We thank the National Natural Science Foundation of China (20732006, 20821002, 21025209), the National Basic Research Program of China (973 Program 2010CB833300), and the Chinese Academy of Sciences for generous financial support.
National Natural Science Foundation of China - No. 20732006; No. 20821002; No. 21025209
National Basic Research Program of China - No. 973 Program 2010CB833300
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ArticleID:ANIE201103937
ark:/67375/WNG-V1QZWZ4X-H
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201103937