Journal of Organic Chemistry p. 5931 - 5943 (1993)
Update date:2022-08-04
Topics:
Molander, Gary A.
Cameron, Kimberly O.
A variety of 1,4- and 1,5-keto aldehydes derived from cycloalkanes are coupled with the bis(trimethylsilyl) enol ether of methyl acetoacetate in the presence of either TMSOTf or TrSbCl6 to generate tricyclic ethers.The reactions proceed with excellent regiochemical control by a mechanism involving neighboring group participation.This mechanism involves initial formation of a bicyclic oxocarbenium ion intermediate from the keto aldehyde substrates.The geometries of selected bicyclic intermediates have been optimized using the AM1 method allowing successful prediction of the stereochemical outcomes in the cyclization in most cases.Epimerization of α-chiral keto aldehyde substrates does not appear to occur in these Lewis acid-promoted annulation reactions.
View MoreBasilea Pharmaceutica China Ltd.
Contact:+86-513-82198075
Address:No.638 Xiushan Road(East),Haimen, Jiangsu 226100, P.R.China
Chongqing Rong&Quan Pharmaceutical Technology Co. , Ltd.
Contact:86-023-65268721
Address:No. 7, Manshanhong Village, Pingdingshan, Shapingba District, Chongqing Province, China
ShangHai Soyoung Biotechnology Inc
website:http://www.soyoungbio.com
Contact:+86-21-69893009
Address:shanghai
Contact:0086-29-89196322
Address:North of the Fifth Keji Road, Hi-Tech Industrial Zone, Xi'an City, Shaanxi Province, China
Xinchang Jiu Xin Pharmaceutical Co., Ltd
website:http://www.jiuxinpharm.com
Contact:86 137 5756 8585
Address:Poyang industry Park
Doi:10.1016/S0957-4166(00)80135-4
(1993)Doi:10.1016/j.electacta.2013.09.063
(2013)Doi:10.1016/S0040-4039(01)99062-8
(1968)Doi:10.1016/j.phytochem.2004.08.026
(2004)Doi:10.1055/s-0033-1339895
(2013)Doi:10.1080/00397919308013802
(1993)