Abstract

γ-Monosubstituted and trans-α,β-disubstituted γ-lactams were diastereoselectively synthesized from common intermediates (S)-N,N-dibenzylated aldehydes derived from natural l-(α)-amino acids, employing a divergent approach. The key features of the routes include diastereoselective Henry and Michael reactions that produced chiral γ-nitroester derivatives, which were subsequently submitted to a tandem reduction-lactamization sequence providing the title compounds. The versatility of routes can allow the preparation of several other mono-, di-, or tri-substituted γ-lactams.

中文翻译：

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（S）-N，N-二苄基-α-氨基醛经亨利和迈克尔反应不同和非对映选择性地合成α-单取代和反式α，β-二取代的γ-内酰胺

摘要

γ-单取代和反式-α，β-二取代的γ-内酰胺采用发散的方法，从天然1-（α）-氨基酸衍生的常见中间体（S）-N，N-二苄基醛中非对映选择性地合成。该途径的关键特征包括产生手性γ-硝基酯衍生物的非对映选择性亨利和迈克尔反应，随后将其进行串联还原-内酰胺化序列，提供标题化合物。路线的通用性可以允许制备其他几种单，双或三取代的γ-内酰胺。