CaltechAUTHORS
Published March 27, 1995 | Version public
Journal Article Metadata-only

Remote Asymmetric Induction in Free-Radical Cycloaddition Leading to Trans-Cyclohexano-Fused 12-Membered Crown Thioethers

Creators

  • 1. ROR icon N.D. Zelinsky Institute of Organic Chemistry
  • 2. ROR icon Moscow State University of Fine Chemical Technologies
  • 3. ROR icon A. N. Nesmeyanov Institute of Organoelement Compounds

Abstract

Homolytic cycloaddition of dithiol 1, derived from trans-1,2-cyclohexanediol, to alkynes induced by Pr3BO2 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

Identifiers

Eprint ID
40887
DOI
10.1016/0040-4039(95)00287-5
Resolver ID
CaltechAUTHORS:20130821-160734870

Funding

Russian Foundation for Fundamental Studies
93-03-18110
Russian Foundation for Fundamental Studies
94-03-09296
International Science Foundation
MPL000

Dates

Created
2013-08-29
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Updated
2021-11-10
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