Journal of Organic Chemistry p. 8197 - 8202 (1994)
Update date:2022-08-02
Topics: Rearrangement Starting Material Workup Catalysis Chiral Control
An, Yi-Zhong
An, Jian Guo
Wiemer, David F.
A series of chiral auxiliaries has been tested for viability in the vinyl phosphate/β-keto phosphonate rearrangement.While dienyl phosphates derived from ephedrine, pseudoephedrine, and isopinocampheol succumbed to competing elimination reactions, ones derived from menthol and (S)-2-methylbutanol were found to undergo rearrangement to the desired β-keto phosphonates.The bis((S)-2-methylbutyl) phosphorochloridate then was used to prepare the vinyl phosphates of the prochiral ketone 4-methylcyclohexanone, and modest diastereoselectivity was observed upon rearrangement of these phosphates to the corresponding β-keto phosphonates.The de of this rearrangement was established by degradation of the β-keto phosphonate to 3-methyladipic acid and determination of the optical rotation.This sequence allowed identification of the major rearrangement product as the 4R-diastereomer of β-keto phosphonate 13.Finally, two other prochiral cyclohexanones were found to be suitable substrates for the vinyl phosphate/β-keto phosphonate rearrangement.
View MoreShanghai Micro-mega Industry Co., Ltd.
Contact:0086-21-34628682;57153848
Address:Rm413,No.413,West Meilong Road, Minhang District,Shanghai P R China
Shanghai Egoal Chemical Co.,Ltd
Contact:+86-21-50333091
Address:Yangming Garden Square 3,YangGao North Road 1188, Pudong New District, Shanghai
Hunan Haili Chemical Industry Co.,Ltd.
Contact:+86-731-85521860
Address:No.251, 2nd Section, Furong Road, Changsha,Hunan,China
Zhejiang Golden-Shell Pharmaceutical Co.,Ltd.
Contact:+86-576-87501888 / 87501988
Address:No.89 Zhongxing Road. Li'ao, Yuhuan, Zhejiang, China
Xinchang Jiu Xin Pharmaceutical Co., Ltd
website:http://www.jiuxinpharm.com
Contact:86 137 5756 8585
Address:Poyang industry Park
Doi:10.1021/ic060756k
(2006)Doi:10.1016/j.ejmech.2014.05.009
(2014)Doi:10.1002/jccs.200900039
(2009)Doi:10.1016/S0957-4166(00)80387-0
(1994)Doi:10.1016/j.bmcl.2021.128059
(2021)Doi:10.1246/cl.2006.918
(2006)