XY–ZH systems as potential 1,3-dipoles. Part 7. Stereochemistry of the cycloaddition of imines of α-amino acid esters to fumarate and maleate esters
- 31 December 1986
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 10,p. 2275-2284
- https://doi.org/10.1039/p19870002275
Abstract
Aryl imines of α-amino acid esters undergo 1,3-dipolar cycloadditions with maleate and fumarate esters in quantitative yield when heated in boiling toluene to give mixtures of mainly two pyrrolidines. The major isomer in each case arises from cycloaddition via an endo-transition state to the same kinetically formed dipole. In aryl imines of methyl phenylglycinate the kinetic dipole undergoes partial stereomutation giving ca. 3:1 mixtures of cycloadducts derived from the kinetic dipole and the stereomutated dipole. Structural assignments are based on 1H n.m.r. data including n.O.e. difference spectroscopy.Keywords
This publication has 3 references indexed in Scilit:
- X=y-zh systems as potential 1,3-dipoles—5Tetrahedron, 1985
- XY–ZH systems as potential 1,3-dipoles. Part 1. Background and scopeJournal of the Chemical Society, Perkin Transactions 1, 1984
- Kinetics and Mechanism of 1,3‐Dipolar CycloadditionsAngewandte Chemie International Edition in English, 1963