Tetrahedron p. 14533 - 14542 (1996)
Update date:2022-07-29
Topics:
Shinokubo, Hiroshi
Oshima, Koichiro
Utimoto, Kiitiro
An addition of benzaldehyde to an ethereal solution of tert-butyldimethylsilyldibromomethyllithium, derived from t-BuMe2SiCHBr2 and lithium diisopropylamide, provided α-bromo-α-silyl ketone. The use of ketone instead of aldehyde afforded α-bromoacylsilane via a bromo silyl epoxide intermediate. Further treatment of the α-bromo-α-silyl ketone with butyllithium afforded lithium enolate which provided β-hydroxy-α-silyl ketone upon treatment with aldehyde in ether. The enolate gave α,β-unsaturated ketone or monosilyl ether of 2-acyl-1,3-diol in THF instead of ether. The use of isopropylmagnesium bromide in place of butyllithium also resulted in a formation of the corresponding magnesium enolate.
View MoreNanjing Zelang Medical Technology Co. Ltd
Contact:86-25-83063290/13770714480
Address:Ganjiabian 108# 01 Unit,701-702 room,Yao Hua Street,Qixia District,Nanjing,Jiangsu,China
Contact:+86-134-5286-9121
Address:Add: Wing Tuck Commercial Centre, 177-183 Wing Lok Street, Hong Kong,
Taizhou Chemedir Biopharm-tech Co., Ltd
Contact:+86 523 86200218
Address:G09, No. 1 Avenue China Medical City, Taizhou,Jiangsu, China
Shenyang Xingzhenghe Chemical Co., Ltd.
Contact:024-23509232
Address:No. 33, Naner Road, Heping Dist.
HANGZHOU PANYU CHEMICAL CO.,LIMITED
Contact:+86-571-86578491
Address:Rm 605, NO.1870 Binsheng Road,Binjiang Dist, Hangzhou, China
Doi:10.1055/s-0035-1561324
(2016)Doi:10.1021/ol500623w
(2014)Doi:10.1002/chem.201202498
(2013)Doi:10.1016/S0040-4039(00)60531-2
(1993)Doi:10.1016/j.ejmech.2019.111866
(2020)Doi:10.1007/s11164-014-1605-x
(2014)