Tetrahedron Asymmetry p. 1209 - 1221 (1991)
Update date:2022-08-05
Topics: Stereochemical Control Chirality transfer Chiral Catalysts Chiral Dienophiles Chiral Diene and Chiral Dienophile
Defoin
Pires
Tissot
Tschamber
Bur
Zehnder
Streith
Diels-Alder reaction of the achiral 1-silyloxybutadiene 1a with the chiral acylnitroso dienophile 2a gave cycloadduct 4 in high diastereomeric excess (d.e. > 98%), a result which is undoubtedly due to the C-2 symmetrical chiral dimethylpyrrolidine inductor. Excellent d.e. was also observed when the (R)-prolinol dienophile 2d was reacted with the chiral diene 1b (d.e. = 96%), whereas cycloaddition of the (S) enantiomer 2e with 1b gave only poor asymmetric induction (d.e. = 4%). These two latter examples nicely illustrate the influence of 'matched pair' (1b/2d) versus 'mismatched pair' (1b/2e) upon double asymmetric induction. All herein reported Diels-Alder cycloadditions were regiospecific.
View MoreWEIFANG RICHEM INTERNATIONAL LTD
Contact:86-536-2222176
Address:weifang,shandong
Contact:+86-25-85281586
Address:13F,Bld2#,South of Longpan Road
website:http://www.eastarchem.com/
Contact:1-800-898-2436
Address:1215 K Street, STE 1700
Hangzhou jls Flame Retardants Chemical Co.,Ltd
Contact:+86-571-87250387/87250386
Address:MOGANSHAN RODA 1418# SHANGCHENG INDUSTRIAL PARK
Jinan Jianfeng Chemical Co., Ltd
Contact:0086-531-88110457
Address:sales01(-a-t-)pharmachemm{dot}c+o+m
Doi:10.1002/chem.201603783
(2016)Doi:10.1016/j.tetlet.2012.06.086
(2012)Doi:10.1016/j.jorganchem.2012.06.004
(2012)Doi:10.1021/ja00050a024
(1992)Doi:10.1021/ja306771n
(2012)Doi:10.1016/0040-4039(92)88059-E
(1992)