Type 2 intramolecular N-acylnitroso Diels-Alder reaction: Scope and application to the synthesis of medium ring lactams

SM Sparks, CP Chow, L Zhu…

Index: Sparks, Steven M.; Chow, Chun P.; Zhu, Liang; Shea, Kenneth J. Journal of Organic Chemistry, 2004 , vol. 69, # 9 p. 3025 - 3035

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Citation Number: 43

Abstract

Heteroatom variants of the type 2 intramolecular Diels-Alder reaction provide an efficient method for the preparation of bridged bicyclic heterocycles. The type 2 variant of the intramolecular N-acylnitroso Diels-Alder reaction is an effective method for the synthesis of bridged bicyclic oxazinolactams. Structural studies of the cycloadducts have allowed for quantification of the deformations of the bridgehead functionalities and provided a strategy ...