Copper(I)-Catalyzed Enantioselective Incorporation of Ketones to Cyclic Hemiaminals for the Synthesis of Versatile Alkaloid Precursors

A general catalytic enantioselective method that can produce five-, six-, and seven-membered N-heterocycles possessing various ketone moieties starting from stable and easily available cyclic hemiaminals and ketones was developed. The method involves three successive steps in one pot (aldol addition...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 134; no. 41; pp. 17019 - 17022
Main Authors Shi, Shi-Liang, Wei, Xiao-Feng, Shimizu, Yohei, Kanai, Motomu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.10.2012
Amer Chemical Soc
Subjects
Alkaloids - chemical synthesis
Alkaloids - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Copper - chemistry
Heterocyclic Compounds - chemistry
Ketones - chemistry
Molecular Structure
Nitrogen - chemistry
Organometallic Compounds - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
AZA-MICHAEL REACTION
ALDOL
PYRROLIDINE
ASYMMETRIC-SYNTHESIS
PIPERIDINE
RING
INDOLIZIDINE
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Summary:A general catalytic enantioselective method that can produce five-, six-, and seven-membered N-heterocycles possessing various ketone moieties starting from stable and easily available cyclic hemiaminals and ketones was developed. The method involves three successive steps in one pot (aldol addition, dehydration, and enantioselective intramolecular aza-Michael reaction), all of which are promoted by a chiral copper(I)-conjugated Brønsted base catalyst. This method is useful for rapid access to versatile chiral building blocks for the synthesis of drug-lead alkaloids.
Bibliography:ObjectType-Article-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja308872z