Journal of Organic Chemistry p. 5058 - 5065 (1990)
Update date:2022-08-05
Topics:
Midland, M. Mark
Koops, Roger W.
The cycloaddition reactions of various α-alkoxy aldehydes with 1,3-dimethoxy-1-<(trimethylsilyl)oxy>-1,3-butadiene (Brassard's diene, 2) were performed under the Lewis acid catalysis of Eu(hfc)3, magnesium dibromide, or diethylaluminum chloride.Moderate to high diastereoselectivities were observed with Eu(hfc)3 and magnesium dibromide.Evidence from reactions of Eu(hfc)3 and magnesium dibromide catalysis indicated a possible "chelation-control" pathway.Lewis acid catalysis from diethylaluminum chloride provides products with moderate to high diastereoselectivity.The mechanistic pathway with catalysis by diethylaluminum chloride was less clear.A possible mechanism based upon a "Cram" addition is considered.
View MoreShanghai Dano Pharmaceutical Co.,Ld.(expird)
Contact:+86-592-6266840
Address:Building 1 Room 512, 720 Cailun Rd, Zhangjiang High-Tech Park, Shanghai 201203, China
shanghai Tauto Biotech Co., Ltd
website:http://www.tautobiotech.com/en/index.htm
Contact:+86-21-51320588 ext. 8025
Address:No. 326, Aidisheng Rd , Zhangjiang Hi-tech Park, Shanghai , P.R.CHINA
Dongguan Albiya Energy Science and Technology Co.,Ltd
Contact:+86-769-22181286
Address:Huanan Industial Park, Dongguan,China
Shanghai Massive Chemical Technology Co., Ltd.
website:http://www.massivechem.com/
Contact:+86 21 34943721
Address:Room 435, 4th floor, Building 9, No. 2568 Gudai Road,Minhang District, Shanghai,
Contact:+86-021-50792271
Address:Building 24A, 300 Chuantu Road, Chuansha, Pudong new area, Shanghai, China, 201202
Doi:10.1002/jhet.5570270311
(1990)Doi:10.1016/j.cclet.2012.06.024
(2012)Doi:10.1002/jhet.5570270307
(1990)Doi:10.1016/j.bmcl.2010.12.037
(2011)Doi:10.1007/s00044-021-02717-6
(2021)Doi:10.1007/BF00963026
(1990)
