Synthesis of optically active spiro-β-lactams by cycloadditions to α-alkylidene-β-lactams

被引：59

作者：

Anklam, S ^{[1
]}

Liebscher, J ^{[1
]}

机构：

[1] Humboldt Univ, Inst Chem, D-10115 Berlin, Germany

来源：

TETRAHEDRON | 1998年 / 54卷 / 23期

关键词：

D O I：

10.1016/S0040-4020(98)00296-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New optically active alpha-methylene-beta-lactam 18 and the alpha-ethylidene-beta-lactams 11-E and 11-Z were synthesized and submitted to 1,3-dipolar cycloadditions with diazomethane, 4-methoxybenzonitrile oxide, and diphenylnitrone as well as to epoxidation by dimethyldioxirane. All cycloadditions proceed with complete regioselectivity giving products 20-25 in an anti-fashion with respect to the substituent at the C-4-position of the starting beta-lactam in diastereomeric ratios of about 80:20. Pure optically active compounds could be obtained in almost all cases after chromatography. Unambiguous structure elucidation could be achieved by X-ray crystal analysis and NOE investigations. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：6369 / 6384

页数：16

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