Metal-promoted allylation, propargylation, or allenylation of azetidine-2,3-diones in aqueous and anhydrous media.: Application to the asymmetric synthesis of densely functionalized 3-substituted 3-hydroxy-β-lactams

被引：72

作者：

Alcaide, B ^{[1
]}

Almendros, P ^{[1
]}

Aragoncillo, C ^{[1
]}

Rodríguez-Acebes, R ^{[1
]}

机构：

[1] Univ Complutense, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 15期

关键词：

D O I：

10.1021/jo015704l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Metal-mediated carbonyl allylation, allenylation, and propargylation of optically pure azetidine-2,3-diones were investigated in both anhydrous and aqueous environments. Different metals promoters showed varied regioselectivities on product formation during allenylation/propargylation reactions of the keto-beta -lactams. The stereochemistry of the new C3-substituted C3-hydroxy quaternary center was controlled by placing a chiral auxiliary at C4. In this way, the coupling of azetidine-2,3-diones with a variety of propenyl-, propynyl-, and allenylmetal reagents offers a convenient asymmetric entry to potentially bioactive 3-substituted 3-hydroxy-beta -lactams.

引用

页码：5208 / 5216

页数：9

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