Bulletin of the Chemical Society of Japan p. 4067 - 4078 (1987)
Update date:2022-08-03
Topics:
Tsuge, Otohiko
Kanemasa, Shuji
Ohe, Masayuki
Yorozu, Kiyotaka
Takenaka, Shigeori
Ueno, Kazunori
Condensation of 2-amino esters with carbonyl compounds leads to simple generation of ester-stabilized azomethine ylides which are trapped by olefinic dipolarophiles as cycloadducts.Anti ylides are exclusively involved in the cycloadditions when N-substituted 2-amino esters are employed for the ylide generation, while syn ylides from N-unsubstituted 2-amino esters.Relative stability among all possible ylide isomers has been inspected and the selective involvement of particular ylidic forms has been explained on the ground of 1,5-dipole interaction or hydrogen bonding stabilization.Endo- and exo-selectivity of the cycloadditions is also discussed.
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Doi:10.1055/s-1987-27919
(1987)Doi:10.1016/S0040-4039(01)81478-7
(1984)Doi:10.1039/b816418e
(2009)Doi:10.1134/S1070427208030269
(2008)Doi:10.1002/chem.201703380
(2017)Doi:10.1021/ja01575a057
(1957)