Journal of the Chemical Society. Perkin transactions I p. 931 - 938 (1996)
Update date:2022-08-03
Topics:
Al-Badri, Hashim
About-Jaudet, Elie
Collignon, Noel
Lithiated α-trimethylsilyl cinnamyl-, prenyl- and crotyl-phosphonate carbanions 4 were generated quantitatively in situ from corresponding phosphonates 1, and their reactions with aldehydes were studied. When reacted at 0 °C with aromatic or aliphatic aldehydes, the cinnamyl derivative 4a gave phosphonodienes 7 in high yield and with high stereoselectivity. In contrast, the prenyl derivative 4b showed strict γ-regioselectivity in its reactions with aromatic aldehydes, leading to cyclic organophosphorus compounds 11; with aliphatic aldehydes, a mixture of corresponding heterocyclic compound 11 as major product, and of phosphonodiene 9, as minor product, was obtained. Reactions of crotyl derivative 4c with aromatic or aliphatic aldehydes were highly γ-regioselective too, and phosphonoalcohols 13 could be isolated upon hydrolysis at -70°C. When warmed near 50°C, alkoxides 12 underwent cyclization reaction to give heterocyclic compounds 14.
View MoreChangzhou BaoKang Pharmaceutical & Chemical Co., Ltd
Contact:(86) 519-88782201 88784080 88785278
Address:Henglin town, changzhou,Jiangsu
Arshine Pharmaceutical Co., Limited
website:http://www.cnarshine.com
Contact:0731-88503671
Address:Room 1109.Block C3, Lugu Enterprise Plaza,No.27 Wenxuan Road,Changsha National Hi-Tech Industrial Development Zone,Hunan ,P.R.China
LIAONING DMSO CHEMICALS CO.,LTD.
website:http://www.chinadmso.com
Contact:+86-427-6503033
Address:FLOOR 16, BLOCK A, FINANCIAL SQUARE, XINGLONGTAI DISTRICT, PANJIN CITY, LIAONING P.R. CHINA
Beijing Stable Chemcial Co.ltd
Contact:86-10-63785052
Address:A1301 Technological Edifice. No.4 FuFeng Road,FengTai District, Beijing. China
Contact:+65 9658 0999
Address:26 Sin Ming Lane, Midview City, #05-118, Singapore 573971
Doi:10.1021/ja00401a028
(1981)Doi:10.1021/jm9604383
(1997)Doi:10.1016/0277-5387(95)00497-1
(1996)Doi:10.1016/0040-4020(96)00318-3
(1996)Doi:10.1016/0040-4039(96)00491-1
(1996)Doi:10.1016/0020-1693(95)04949-5
(1996)
