Remote Asymmetric Induction in Free Radical Cycloaddition Leading to Trans-cyclohexano-fused 12-membered Crown Thioethers
- Troyansky, Emmanuil I
- Ismagilov, Rustem F.
- Strelenko, Yury A.
- Samoshin, Vyacheslav V.
- Demchuk, Dmitry V.
- Nikishin, Gennady I.
- Lindeman, Sergey V.
- Khrustalyov, Viktor N.
- Struchkov, Yury T.
DOIAbstract
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. Homolytic cycloaddition of trans-1,2-bis(mercaptoacetoxy)cyclohexane1 to alkynes 3 occurs with 1,6-asymmetric induction to afford predominantly (1S*, 6R*, 12S*)-trans-cyclohexano-fused 12-membered crown thialactone
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