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Enantioselective (formal) aza-Diels-Alder reactions with non-Danishefsky-type dienes.

ABSTRACT: Enantioselective (formal) aza-Diels-Alder reactions between acylhydrazones and non-Danishefsky-type dienes have been developed. The reactions are promoted by a simple and economical chiral silicon Lewis acid and are typically conducted at ambient temperature. Both glyoxylate- and aliphatic aldehyde-derived hydrazones may be employed, as may variously substituted dienes, leading to the synthesis of a diverse array of tetrahydropyridines with good to excellent levels of enantioselectivity.

SUBMITTER: Tambar UK

PROVIDER: S-EPMC2918383 | biostudies-literature | 2010 Aug

REPOSITORIES: biostudies-literature

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Enantioselective (formal) aza-Diels-Alder reactions with non-Danishefsky-type dienes.

Tambar Uttam K UK Lee Sharon K SK Leighton James L JL

Journal of the American Chemical Society 20100801 30

Enantioselective (formal) aza-Diels-Alder reactions between acylhydrazones and non-Danishefsky-type dienes have been developed. The reactions are promoted by a simple and economical chiral silicon Lewis acid and are typically conducted at ambient temperature. Both glyoxylate- and aliphatic aldehyde-derived hydrazones may be employed, as may variously substituted dienes, leading to the synthesis of a diverse array of tetrahydropyridines with good to excellent levels of enantioselectivity. ...[more]

PMID: 20662502

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