The Journal of Organic Chemistry

Oxidative cyclization of. delta.,. epsilon.-and. epsilon.,. zeta.-unsaturated enol silyl ethers and unsaturated siloxycyclopropanes

BB Snider, T Kwon

Index: Snider, Barry B.; Kwon, Taesoo Journal of Organic Chemistry, 1992 , vol. 57, # 8 p. 2399 - 2410

Full Text: HTML

Citation Number: 74

Abstract

Oxidative cyclization of &e-and e,{-unsaturated enol silyl ethers 4a and 4b with cupric triflate and cuprous oxide or ceric ammonium nitrate and sodium bicarbonate in acetonitrile provides the tricyclic ketones 5a and 5b stereoselectively. These cyclizations proceed by oxidation of 4 to the cation radical 24 followed by cyclization of 24 to cation radical 27. This cation radical undergoes a second cyclization to give cation radical 30, which loses the ...