Synthesis and Rearrangement of  N ‐Organyloxy β‐Lactams Derived from a (4+2)/(3+2) Sequential Cycloaddition Reaction Involving Enol Ethers and Nitro Alkenes | Zendy

van Berkom Leon W. A. | Zendy; Kuster George J. T. | Zendy; de Gelder René | Zendy; Scheeren Hans W. | Zendy

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Synthesis and Rearrangement of N ‐Organyloxy β‐Lactams Derived from a (4+2)/(3+2) Sequential Cycloaddition Reaction Involving Enol Ethers and Nitro Alkenes

Author(s) -

van Berkom Leon W. A.,

Kuster George J. T.,

de Gelder René,

Scheeren Hans W.

Publication year - 2004

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200400371

Subject(s) - chemistry , dimethylamine , nitroso , cycloaddition , lactam , stereochemistry , sigmatropic reaction , enol , nitro , combinatorial chemistry , medicinal chemistry , catalysis , organic chemistry , alkyl

The synthesis of N ‐organyloxy β‐lactams 2 by treatment of nitroso acetals 1 with a base is discussed. Based on the formation of a by‐product, a mechanism for the rearrangement to N ‐organyloxy β‐lactams is proposed. This mechanism is supported by trapping of the intermediate acyl nitro compound 8 with dimethylamine. Furthermore, it was discovered that upon more forcing basic conditions these N ‐organyloxy β‐lactams can rearrange further to 3‐organyloxy β‐lactams. By using a series of structurally diverse N ‐organyloxy β‐lactams the generality of this novel rearrangement is demonstrated. A mechanism for the conversion of N ‐organyloxy β‐lactams to 3‐organyloxy β‐lactams is proposed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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