Bulletin of the Chemical Society of Japan p. 2357 - 2362 (1980)
Update date:2022-07-31
Topics:
Itoh, Akira
Ozawa, Shuji
Oshima, Koichiro
Sasaki, Shizuka
Yamamoto,Hajime
et al.
The reaction of cis- or trans-5-isopropenyl-2-methyl-2-cyclohexenyl diethyl phosphate (1) with Me2AlX (X= OPh, SPh, NHPh) in hexane results in substitution of the -O-PO(OEt)2 group with X under predominant inversion.In contrast, treatment of cis- or trans-1 with trialkylaluminum produces predominantly the allyl-nonallyl coupling products of the same (thermodynamically more stable) configuration.Similar alkylation of endo- and exo-2-acetoxynorcarane gave endo-2-methylnorcarane, exclusively.
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Doi:10.1016/S0040-4039(00)71464-X
(1980)Doi:10.1016/S0040-4039(00)92856-9
(1980)Doi:10.1248/cpb.54.1304
(2006)Doi:10.1021/ja01117a046
(1953)Doi:10.1021/ja01224a024
(1945)Doi:10.1002/ejoc.201501501
(2016)
