Remote Asymmetric Induction in Free Radical Cycloaddition Leading to Trans-cyclohexano-fused 12-membered Crown Thioethers
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 thialactones
Troyansky, Emmanuil I.; Ismagilov, Rustem F.; Strelenko, Yury A.; Samoshin, Vyacheslav V.; Demchuk, Dmitry V.; Nikishin, Gennady I.; Lindeman, Sergey V.; Khrustalyov, Viktor N.; and Struchkov, Yury T., "Remote Asymmetric Induction in Free Radical Cycloaddition Leading to Trans-cyclohexano-fused 12-membered Crown Thioethers" (1995). Chemistry Faculty Research and Publications. 650.