Direct Enantioselective Vinylogous Mannich Reaction of Ketimines with γ-Butenolide by Using Cinchona Alkaloid Amide/Zinc(II) Catalysts

A direct enantioselective vinylogous Mannich reaction of ketimines with γ‐butenolide has been developed. Good yields and enantioselectivities were observed for the reaction of various ketimines by using a cinchona alkaloid amide/Zn(OTf)2 catalyst and Et3N. Both enantiomers of the products could be o...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry : a European journal 2015-06, Vol.21 (27), p.9615-9618
Main Authors: Nakamura, Shuichi, Yamaji, Ryota, Hayashi, Masashi
Format: Article
Language:English
Subjects:
4-Butyrolactone - analogs & derivatives
4-Butyrolactone - chemical synthesis
4-Butyrolactone - chemistry
Alkaloids
Amides
asymmetric synthesis
Catalysis
Catalysts
cinchona alkaloids
Cinchona Alkaloids - chemical synthesis
Cinchona Alkaloids - chemistry
Enantiomers
Imines
Imines - chemistry
ketimines
Lewis acids
Mesylates - chemistry
Molecular Structure
Nitriles - chemistry
Stereoisomerism
γ-butenolides
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A direct enantioselective vinylogous Mannich reaction of ketimines with γ‐butenolide has been developed. Good yields and enantioselectivities were observed for the reaction of various ketimines by using a cinchona alkaloid amide/Zn(OTf)2 catalyst and Et3N. Both enantiomers of the products could be obtained by using pseudoenantiomeric chiral catalysts. A direct enantioselective vinylogous Mannich reaction of ketimines with γ‐butenolide has been developed. Good yields and enantioselectivities were observed for the reaction of various ketimines by using a cinchona alkaloid amide/Zn(OTf)2 catalyst and Et3N (see scheme; Tf=triflate). Both enantiomers of the products could be obtained by using pseudoenantiomeric chiral catalysts.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201500599