
Please use this identifier to cite or link to this item:
http://hdl.handle.net/123456789/1729
Title: | Diastereoselective Desymmetrization of Prochiral Cyclopentenediones via Cycloaddition Reaction with N-Phenacylbenzothiazolium Bromides |
Authors: | Joshi, Mayank |
Keywords: | Anions Desymmetrization Stereoselectivity Addition reactions |
Issue Date: | 2017 |
Publisher: | ACS Publications |
Citation: | Journal of Organic Chemistry, 82 (23) |
Abstract: | A metal-free highly diastereoselctive [3 + 2] cycloaddition reaction has been developed between N-phenacylbenzothiazolium bromides and prochiral cyclopentene-1,3-diones. The active 1,3 dipole benzothiazolium N-phenacylide was generated in situ with the treatment of DIPEA, and the corresponding cycloaddition products were obtained in excellent yields under mild reaction conditions. The scope of the reaction is quite broad, tolerating a variety of aryl and heteroaromatic groups. A catalytic asymmetric approach was also studied preliminarily, and moderate enantioselectivity was achieved. |
URI: | https://pubs.acs.org/doi/10.1021/acs.joc.7b01964 http://hdl.handle.net/123456789/1729 |
Appears in Collections: | Research Articles |
Files in This Item:
File | Description | Size | Format | |
---|---|---|---|---|
Need to add pdf.odt | 8.63 kB | OpenDocument Text | View/Open |
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.