Published March 27, 1995
| public
Journal Article
Remote Asymmetric Induction in Free-Radical Cycloaddition Leading to Trans-Cyclohexano-Fused 12-Membered Crown Thioethers
Abstract
Homolytic cycloaddition of dithiol 1, derived from trans-1,2-cyclohexanediol, to alkynes induced by Pr3BO2 occurs with 1,6-asymmetric induction to afford predominantly (1S∗, 6R∗, 12S∗)-trans-cyclohexano-fused 12-membered crown thialactones 4a-c. No pronounced diasteroselectivity was found in the corresponding reactions of dithiol 2, derived from cis-1,2-cyclohexanediol.
Additional Information
Copyright © 1995 Elsevier. Received 1 November 1994. Accepted 3 February 1995. Available online 14 June 2000. We are grateful to Mr. R. Fleming (The University of Nottingham, U.K.) for recording several NMR spectra. We also thank the Russian Foundation of Fundamental Studies (Projects 93-03-18110 and 94-03-09296) and Intemational Science Foundation (Soros Foundation) (Grant MPL 000) for generous financial support.Additional details
- Eprint ID
- 40887
- DOI
- 10.1016/0040-4039(95)00287-5
- Resolver ID
- CaltechAUTHORS:20130821-160734870
- 93-03-18110
- Russian Foundation for Fundamental Studies
- 94-03-09296
- Russian Foundation for Fundamental Studies
- MPL000
- International Science Foundation
- Created
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2013-08-29Created from EPrint's datestamp field
- Updated
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2021-11-10Created from EPrint's last_modified field