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 ...
Related Articles:
Rhodium-catalyzed methylenation of aldehydes
[Lebel, Helene; Paquet, Valerie Journal of the American Chemical Society, 2004 , vol. 126, # 1 p. 320 - 328]
[Ochiai, Masahito; Ukita, Tatsuzo; Nagao, Yoshimitsu; Fujita, Eiichi Journal of the Chemical Society, Chemical Communications, 1984 , # 15 p. 1007 - 1008]
Copper-Catalyzed Oxaziridine-Mediated Oxidation of C–H Bonds
[Motiwala, Hashim F.; Guelgeze, Belgin; Aube, Jeffrey Journal of Organic Chemistry, 2012 , vol. 77, # 16 p. 7005 - 7022]
Dimerization and Isomerization Reactions of α-Lithiated Terminal Aziridines
[Hok, Saphon; Schore, Neil E. Journal of Organic Chemistry, 2006 , vol. 71, # 4 p. 1736 - 1738]
Dimerization and Isomerization Reactions of α-Lithiated Terminal Aziridines
[Hok, Saphon; Schore, Neil E. Journal of Organic Chemistry, 2006 , vol. 71, # 4 p. 1736 - 1738]