Shee, S and Mukherjee, S and Gonnade, RG and Biju, AT (2020) Enantioselective Synthesis of Tricyclic β-Lactones by NHC-Catalyzed Desymmetrization of Cyclic 1,3-Diketones. In: Organic Letters, 22 (14). pp. 5407-5411.
PDF
ORG_LET_22_14_5407-5411_2020.pdf - Published Version Restricted to Registered users only Download (1MB) | Request a copy |
||
|
PDF
ol0c01756_si_001.pdf - Published Supplemental Material Download (8MB) | Preview |
Abstract
The NHC-catalyzed desymmetrization of cyclic-1,3-diketones allowing the enantioselective construction of tricyclic β-lactones with five contiguous stereocenters, including two quaternary stereocenters, has been developed. The mild and operationally simple addition of α-bromoenals to cyclopentane-1,3-diketone derivatives proceeds via the initial formation of chiral α,β-unsaturated acylazolium intermediates and culminates in a cascade reaction, following the Michael-aldol-lactonization pathway to deliver the β-lactone derivatives in moderate to good yields and excellent selectivity. © 2020 American Chemical Society.
Item Type: | Journal Article |
---|---|
Publication: | Organic Letters |
Publisher: | American Chemical Society |
Additional Information: | copy right for this article belongs to American Chemical Society |
Department/Centre: | Division of Chemical Sciences > Organic Chemistry |
Date Deposited: | 11 Nov 2020 06:28 |
Last Modified: | 11 Nov 2020 06:28 |
URI: | http://eprints.iisc.ac.in/id/eprint/66119 |
Actions (login required)
View Item |