1,4-Addition of (Diphenylmethylene)amine to Acceptor Substituted Olefins. A Versatile Synthesis of Protected β-Amino Acids, Nitriles, and Ketones

Ludger Wessjohann; Gregory Mcgaffin; Armin de Meijere

doi:10.1055/s-1989-27252

Synthesis 1989; 1989(5): 359-363
DOI: 10.1055/s-1989-27252

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1,4-Addition of (Diphenylmethylene)amine to Acceptor Substituted Olefins. A Versatile Synthesis of Protected β-Amino Acids, Nitriles, and Ketones

Ludger Wessjohann^* , Gregory Mcgaffin, Armin de Meijere

^*Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King- Platz 6, D-2000 Hamburg 13, Federal Republic of Germany

Abstract

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(Diphenylmethylene)amine [benzophenone imine, DPMA-H] cleanly reacts with a variety of α,β-unsaturated esters, nitriles, ketones, and aldehydes 1a-q to give Michael type adducts 2a-q, generally, in respectable to excellent yields. Sterically congested and donor-substituted Michael acceptors do not react. The β-amino-substituted products can be further transformed in their protected form, or selectively deprotected under mild conditions, e.g. by catalytic hydrogenation.

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