Abstract

The enantiospecific synthesis of 3-acetoxy-trans-β-lactams via the Staudinger [2+2] cycloaddition reaction of polyaromatic imines with bicyclic (+)-car-3-ene was investigated. The sterically hindered polyaromatic substituent at the N¹ position in the imines plays a significant role, directing the cycloaddition reaction to stereoselective formation of trans-(3R,4R)-N-azetidin-2-ones. The results as described herein are highly unprecedented, since the synthesis of a single optically active trans-β-lactam, starting from a chiral ketene, has never been reported previously.

中文翻译：

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微波诱导的（+）-Car-的Staudinger环加成反应合成反式-（3 R，4 R）-3-乙酰氧基-4-芳基-1-（chrysen-6-基）氮杂环丁烷-2-酮3-烯与多芳香亚胺

摘要

研究了多芳族亚胺与双环（+）-car-3-ene的斯托丁格[2 + 2]环加成反应对3-乙酰氧基-反式-β-内酰胺的对映体特异性合成。亚胺的N ¹位上的位阻多芳族取代基起着重要作用，将环加成反应导向反式-（3 R，4 R）-N-氮杂环丁烷-2-酮的立体选择形成。本文所述的结果是高度前所未有的，因为以前从未报道过从手性烯酮开始合成单个旋光的反式-β-内酰胺。