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■ Enantioselective Synthesis of β-Amino Acids. 5. Stereoselective Reaction of Chiral Pyrimidinone Enolates with Aldehydes

Peter Murer, Beat Rheiner, Eusebio Juaristi, and Dieter Seebach*

*Laboratorium fur Organische Chemie, Eidgenossischen Technischen Hochschule, ETH-Zentrum, Universitatstrasse 16 CH-8092 Zurich, Switzerland

Abstract

Hydro-pyrimidinones ((2S,6R)-3) and ((2S)-6) were prepared from methyl crotonate via 3-aminobutanoate, and their corresponding lithium enolate and dienolate derivatives were added to various aldehydes. The high regio- and stereoselectivities observed in these aldol reactions pave the road for the preparation of enantiomerically pure β-hydroxy-β’-amino acids. The structures of the products were confirmed by X-ray crystal structure analysis (eight examples).