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Synlett 2000; 2000(5): 0707-0709
DOI: 10.1055/s-2000-6635
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An Efficient Preparation of α-Alkylidene-β-formylmethyl-γ-lactams via Pd(II)-Catalyzed Intramolecular Alkyne-α,β-Unsaturated Carbonyl Coupling

Xu Xie* , Xiyan Lu
  • *Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China; Fax 86-21-64166128; E-mail: xylu@pub.sioc.ac.cn
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Publication Date:
31 December 2000 (online)

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An efficient stereoselective cyclization method by palladium(II)-catalyzed intramolecular enyne coupling of N-(3′-formylallylic) alkynamides was developed to yield α-alkylidene-β-formylmethyl-γ-lactams. The substitution pattern of the triple bond determines the β,γ-relative stereochemistry of the lactam product.

coupling - diastereoselectivity - enynes - lactams - palladium