Simple Generation of Ester-Stabilized Azomethine Ylides from 2-Amino Esters and Carbonyl Compounds. Stereochemistry of Their Cycloadditions
- 1 November 1987
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 60 (11) , 4067-4078
- https://doi.org/10.1246/bcsj.60.4067
Abstract
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.This publication has 18 references indexed in Scilit:
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