Journal of the Chemical Society. Perkin transactions I p. 3067 - 3072 (1995)
Update date:2022-08-17
Topics:
Broom, Nigel
O'Hanlon, Peter J.
Simpson, Thomas J.
Stephen, Rosamund
Willis, Christine L.
Treatment of cis-2-oxabicyclo<3.3.0>oct-6-en-3-one 1 with osmium tetraoxide under a variety of conditions led predominantly to attack from the more hindered face of the alkene to give, after protection of the diol, the endo-acetonide 8 as the major product.It is apparent that the stereochemical outcome of this reaction is due to a directing effect from the lactone carbonyl at C-3 since osmylation of the analogous lactols 3, acetals 4 and cyclic ethers 5 gave attack mainly from the less hindered exo-face.The exo-acetonide 7 was prepared in a 3-stage procedure from cis-bicyclo<3.2.0>heptenone 6 in 54percent yield.In this case the stereoselectivity of the osmylation reaction was governed, as espected, by the conformation of the bicyclic skeleton, no directing effect from the ketone carbonyl was apparent.
View Morewebsite:http://www.win-winchemical.com
Contact:0086-577-64498589
Address:6F,No.396 Xingping Road,Longwan Industrial Zone
Yingkou Sanzheng Organic Chemical Co. Ltd.
Contact:+86-417-3638818
Address:25 Gengxinli Village, Daqing Road, Yingkou, Liaoning, China
website:http://www.chinabarton.com
Contact:+86-573-82719618
Address:No. 162 Fumin Road, Honghe Town,
Beijing Stable Chemcial Co.ltd
Contact:86-10-63785052
Address:A1301 Technological Edifice. No.4 FuFeng Road,FengTai District, Beijing. China
Geen Chemical Technology Co., Ltd
Contact:86-769-21660847
Address:1408, Yingfeng Commercial Center, Nancheng District
Doi:10.1007/BF03028081
(1895)Doi:10.1016/j.tet.2019.130765
(2019)Doi:10.1246/bcsj.58.481
(1985)Doi:10.1016/0040-4039(96)00429-7
(1996)Doi:10.1063/1.120724
(1998)Doi:10.1039/c39900001098
(1990)