Enantioselective Vinylogous Mannich Reaction of Acyclic Vinylketene Silyl Acetals with Acyclic Ketimines

The first enantioselective vinylogous Mannich reaction of acyclic vinylketene silyl acetals with acyclic ketimines derived from alkynyl ketoesters was developed. Excellent yields and enantioselectivities were obtained from the reaction using bis(imidazoline)‐Zn(II) catalyst. Based on experiments and...

Full description

Saved in:
Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 363; no. 19; pp. 4544 - 4548
Main Authors Ogura, Kazuki, Takehara, Tsunayoshi, Suzuki, Takeyuki, Nakamura, Shuichi
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 05.10.2021
Wiley Subscription Services, Inc
Subjects
Acetals
Amides
Amines
Carbonyl compounds
Carbonyls
Chemistry
Chemistry, Applied
Chemistry, Organic
Chiral amine
Enantiomers
Enantioselectivity
Imidazoline
Imines
Ketimines
Lewis acids
Physical Sciences
Science & Technology
Stereoselectivity
Vinylogous Mannich reaction
ALPHA,ALPHA-DICYANOOLEFINS
2H-AZIRINES
Enantioselectivity
Ketimines
Lewis acids
ACID HALF THIOESTERS
KETONES
STEREOCENTERS
GAMMA-BUTENOLIDES
CONSTRUCTION
Chiral amine
FRIEDEL-CRAFTS REACTION
Vinylogous Mannich reaction
ALPHA-ISOCYANOACETATES
ALKALOIDS
Online AccessGet full text

Cover

More Information
Summary:The first enantioselective vinylogous Mannich reaction of acyclic vinylketene silyl acetals with acyclic ketimines derived from alkynyl ketoesters was developed. Excellent yields and enantioselectivities were obtained from the reaction using bis(imidazoline)‐Zn(II) catalyst. Based on experiments and MO calculation, a plausible transition state was proposed to explain the stereoselectivity of the reaction. The obtained products were converted into various amines and a lactam. This process provides an efficient route for the synthesis of acyclic δ‐amino‐α,β‐unsaturated carbonyl compounds and their derivatives.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202100872