Cinchona Alkaloid Amides/Dialkylzinc Catalyzed Enantioselective Desymmetrization of Aziridines with Phosphites

The first highly enantioselective desymmetrization of aziridines with phosphites has been developed. Excellent yields and enantioselectivities were observed for the reaction with various aziridines using a new class of readily accessible chiral catalysts derived from 9-amino-9-deoxy-epi-cinchona alk...

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Published inJournal of the American Chemical Society Vol. 134; no. 47; pp. 19366 - 19369
Main Authors Hayashi, Masashi, Shiomi, Noriyuki, Funahashi, Yasuhiro, Nakamura, Shuichi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 28.11.2012
Amer Chemical Soc
Subjects
Amides - chemistry
Aziridines - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Cinchona Alkaloids - chemistry
Models, Molecular
Molecular Structure
Organometallic Compounds - chemistry
Organophosphonates - chemical synthesis
Organophosphonates - chemistry
Phosphites - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
Zinc - chemistry
DESIGN
ALDOL REACTION
IMINES
ASYMMETRIC BIFUNCTIONAL CATALYSIS
HYDROPHOSPHONYLATION
DECARBOXYLATION
BETA-LACTAMS
NITROALKENES
AMINO-ACID-DERIVATIVES
MICHAEL ADDITION
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Summary:The first highly enantioselective desymmetrization of aziridines with phosphites has been developed. Excellent yields and enantioselectivities were observed for the reaction with various aziridines using a new class of readily accessible chiral catalysts derived from 9-amino-9-deoxy-epi-cinchona alkaloids. In studies probing the reaction mechanism, we observed some complexes for the cinchona alkaloid amide-Zn(II) by ESI-MS analysis.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja309963w