Enantioselective synthesis of tricyclic beta-lactones by NHC-catalyzed desymmetrization of cyclic 1,3-diketones

TitleEnantioselective synthesis of tricyclic beta-lactones by NHC-catalyzed desymmetrization of cyclic 1,3-diketones
Publication TypeJournal Article
Year of Publication2020
AuthorsShee, S, Mukherjee, S, Gonnade, RG, Biju, AT
JournalOrganic Letters
Volume22
Issue14
Pagination5407-5411
Date PublishedJUL
Type of ArticleArticle
ISSN1523-7060
Abstract

The NHC-catalyzed desymmetrization of cyclic-1,3-diketones allowing the enantioselective construction of tricyclic beta-lactones with five contiguous stereocenters, including two quaternary stereocenters, has been developed. The mild and operationally simple addition of a-bromoenals to cyclopentane-1,3-diketone derivatives proceeds via the initial formation of chiral alpha,beta-unsaturated acylazolium intermediates and culminates in a cascade reaction, following the Michael-aldol-Iactonization pathway to deliver the beta-lactone derivatives in moderate to good yields and excellent selectivity.

DOI10.1021/acs.orglett.0c01756
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

6.091

Divison category: 
Center for Material Characterization (CMC)

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