Organocatalytic, δ-Regioselective, and Highly Enantioselective Nucleophilic Substitution of Cyclic Morita-Baylis-Hillman Alcohols with Indoles

The unexpected becomes possible: The first enantioselective, direct nucleophilic substitution of Morita–Baylis–Hillman alcohols has been developed through the use of iminium catalysis. Unexpected δ‐substituted products were obtained with exclusive regioselectivity and high enantioselectivity for the...

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Published inAngewandte Chemie (International ed.) Vol. 49; no. 40; pp. 7294 - 7298
Main Authors Qiao, Zhen, Shafiq, Zahid, Liu, Li, Yu, Zheng-Bao, Zheng, Qi-Yu, Wang, Dong, Chen, Yong-Jun
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 24.09.2010
WILEY-VCH Verlag
WILEY‐VCH Verlag
Wiley
Subjects
Chemistry
Chemistry, Multidisciplinary
indoles
Morita-Baylis-Hillman alcohols
nucleophilic substitution
organocatalysis
Physical Sciences
Science & Technology
δ regioselectivity
SIMPLE ALPHA,BETA-UNSATURATED KETONES
ACTIVATED ALLYLIC ACETATES
FURAQUINOCIN-E
CONJUGATE ADDITION-ELIMINATION
delta regioselectivity
Morita-Baylis-Hillman alcohols
MICHAEL ADDITION
CASCADE REACTION
organocatalysis
indoles
nucleophilic substitution
KINETIC RESOLUTION
GAMMA-BUTENOLIDES
ASYMMETRIC AMINOCATALYSIS
FRIEDEL-CRAFTS ALKYLATION
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Summary:The unexpected becomes possible: The first enantioselective, direct nucleophilic substitution of Morita–Baylis–Hillman alcohols has been developed through the use of iminium catalysis. Unexpected δ‐substituted products were obtained with exclusive regioselectivity and high enantioselectivity for the reaction of cyclopent‐2‐enone‐derived alcohols with indoles catalyzed by 1.
Bibliography:http://dx.doi.org/10.1002/anie.201003131
ArticleID:ANIE201003131
Chinese Academy of Sciences
ark:/67375/WNG-1NJJSLP8-B
2009ZX09501-006
The research was financially supported by the National Natural Science Foundation of China, Ministry of Science and Technology (Nos. 2009ZX09501-006 and 2010CB833305) and the Chinese Academy of Sciences.
istex:E7650AD59961A7D1803DC23B05C0BEBE63F59116
2010CB833305
National Natural Science Foundation of China, Ministry of Science and Technology
The research was financially supported by the National Natural Science Foundation of China, Ministry of Science and Technology (Nos. 2009ZX09501‐006 and 2010CB833305) and the Chinese Academy of Sciences.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201003131