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Improved dienophilicity of nitrocycloalkenes: prospects for the development of a trans-Diels-Alder paradigm.

ABSTRACT: The development of an efficient and stereoselective trans-Diels-Alder paradigm is described. A central element of this transformation is the introduction of a temporary dienophilic functionality (A), which serves both to activate the substrate for Diels-Alder cycloaddtion and, through its subsequent removal, to facilitate conversion of the cis-fused cycloadducts to the trans-fused series.

SUBMITTER: Kim WH

PROVIDER: S-EPMC2746560 | biostudies-literature | 2009 Sep

REPOSITORIES: biostudies-literature

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Improved dienophilicity of nitrocycloalkenes: prospects for the development of a trans-Diels-Alder paradigm.

Kim Woo Han WH Lee Jun Hee JH Danishefsky Samuel J SJ

Journal of the American Chemical Society 20090901 35

The development of an efficient and stereoselective trans-Diels-Alder paradigm is described. A central element of this transformation is the introduction of a temporary dienophilic functionality (A), which serves both to activate the substrate for Diels-Alder cycloaddtion and, through its subsequent removal, to facilitate conversion of the cis-fused cycloadducts to the trans-fused series. ...[more]

PMID: 19685875

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