Troyansky, Emmanuil I. and Ismagilov, Rustem F. and Strelenko, Yury A. and Samoshin, Vyacheslav V. and Demchuk, Dmitry V. and Nikishin, Gennady I. and Lindeman, Sergey V. and Khrustalyov, Viktor N. and Struchkov, Yury T. (1995) Remote Asymmetric Induction in Free-Radical Cycloaddition Leading to Trans-Cyclohexano-Fused 12-Membered Crown Thioethers. Tetrahedron Letters, 36 (13). pp. 2293-2294. ISSN 0040-4039. doi:10.1016/0040-4039(95)00287-5. https://resolver.caltech.edu/CaltechAUTHORS:20130821-160734870
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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.
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| 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. | |||||||||
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| Subject Keywords: | macrocyclization; construction; alkynes; route | |||||||||
| Issue or Number: | 13 | |||||||||
| DOI: | 10.1016/0040-4039(95)00287-5 | |||||||||
| Record Number: | CaltechAUTHORS:20130821-160734870 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20130821-160734870 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 40887 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Whitney Barlow | |||||||||
| Deposited On: | 29 Aug 2013 21:45 | |||||||||
| Last Modified: | 10 Nov 2021 04:23 |
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