手性有机铜（手性恶唑啉）催化剂催化下，端基炔和硝酮进行偶极环加成得到异恶唑啉中间体，重排后得到立体选择性的β-内酰胺的反应。
反应机理
反应实例
(3S, 4S)-1,3,4-Triphenyl-2-azetidinone (5). (S)-trisoxazoline 6 (11.3 mg, 0.03 mmol) and Cu(ClO4)2.H2O (9.3 mg, 0.025 mmol) in 4 mL MeCN were stirred for 2 h at 15 C. After cooling to 0 C, dicyclohexylamine (0.25 mmol) was added, followed after 10 min by phenylacetylene 1 (38 mg, 0.375 mmol). The color turned yellow and 0.25 mmol of nitrone 2 was added. The reaction was monitored by TLC and after 35 h the mixture was first filtered over silica gel using DCM as eluent and the solvent evaporated. Flash chromatography (PE/DCM) gave b-lactam 5 in 56% yield,[a]20 D ¼ 8.0 (c ¼1.62, CHCl3) and 82%ee.
【Tang Y, J Org Chem, 2006, 71, 3576】
相关文献
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编译自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 259.
相关反应
Breckport β-内酰胺合成
