Organocatalytic Enantioselective (4+2) Annulation of Cyclopropane Carbaldehydes with 2‐Mercapto‐1‐Arylethanones

Here, we report the organocatalytic enantioselective synthesis of dihydrothiopyran derivatives from trans racemic donor–acceptor cyclopropane carbaldehydes (DACCs) and 2‐mercapto‐1‐arylethanone via formal thio (4+2) cycloaddition involving thia‐Michael aldol condensation and annulation. Mechanistic...

Full description

Saved in:
Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 366; no. 5; pp. 1113 - 1119
Main Authors Yadav, Neeraj, Hazra, Arijit, Singh, Priyanka, Banerjee, Prabal
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 08.03.2024
Wiley Subscription Services, Inc
Subjects
(4+2) annulation
Aldehydes
Asymmmetric organocatalysis
Chemical reactions
Chemistry
Chemistry, Applied
Chemistry, Organic
Cycloaddition
Cyclopropane
Enantiomers
kinetic resolution
Organic chemistry
Physical Sciences
Science & Technology
thia-Michael aldol condensation
thia-Michael aldol condensation
DONOR-ACCEPTOR CYCLOPROPANES
TETRAHYDROTHIOPHENES
SULFA-MICHAEL/MICHAEL ADDITION
ASYMMETRIC-SYNTHESIS
STRATEGY
GOLDEN-AGE
CASCADE
(4+2) annulation
DOUBLE-MICHAEL-ADDITION
Asymmmetric organocatalysis
kinetic resolution
CYCLOADDITION REACTION
DERIVATIVES
Online AccessGet full text

Cover

More Information
Summary:Here, we report the organocatalytic enantioselective synthesis of dihydrothiopyran derivatives from trans racemic donor–acceptor cyclopropane carbaldehydes (DACCs) and 2‐mercapto‐1‐arylethanone via formal thio (4+2) cycloaddition involving thia‐Michael aldol condensation and annulation. Mechanistic studies indicate a typical kinetic resolution (KR) is involved in this transformation, which results in moderate yields and enantiomeric ratios. Remarkably, this method is characterized by its one‐pot simplicity, mild reaction conditions, and resilience towards air and moisture interference.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202301187