Addition of Chiral Glycine, Methionine, and Vinylglycine Enolate Derivatives to Aldehydes and Ketones in the Preparation of Enantiomerically Pure α‐Amino‐β‐Hydroxy Acids

作者：Dieter Seebàch, Eusebio Juaristi, David D. Miller, Christof P. Schickli, THEODOR H. WEBER · 发表于：Helvetica Chimica Acta · 年份：1987 · DOI：10.1002/hlca.19870700129 · 被引用次数：197 · 研究领域：Fluorine in Organic Chemistry、Chemical Synthesis and Analysis、Carbohydrate Chemistry and Synthesis

Abstract Chiral enolates of imidazolidinones and oxazolidinones from the title amino acids react with carbonyl compounds to afford the corresponding alcohols in excellent yields (see Scheme 5). Furthermore, the addition to aldehydes proceeds with high diastereoselectivity to give, after acid hydrolysis, threo‐α‐amino‐β‐hydroxy acids of high enantiomeric purity. Some of the threo‐α‐amino‐β‐hydroxy acids prepared in this work are the proteinogenic (S)‐threonine (26), the naturally occurring (S)‐3‐phenylserine (28), and (S)‐3‐hydroxyleucine (27) as well as the unnatural (S)‐4,4,4‐trifluorothreonine (30) and (S)‐3‐(4‐pyridyl)serine (31). The N‐methylamide of (2S,3R,4R,6E)‐3‐hydroxy‐4‐methyl‐2‐(methylamino)‐6‐octenoic acid (32), the unique amino acid in the immunosuppressive cyclosporine, was prepared by the new method. This report presents also information suggesting that both steric and stereoelectronic effects are responsible for the good stereoselectivities observed.