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Synthesis of isoquinuclidines from highly substituted dihydropyridines via the Diels-Alder reaction.

ABSTRACT: A stereo- and regioselective Diels-Alder reaction for the synthesis of highly substituted isoquinuclidines from dihydropyridines and electron-deficient alkenes has been developed. While reactions with activated dienophiles proceed readily under thermal conditions, the use of Lewis acid additives is necessary to facilitate cycloadditions for less reactive alkenes. This procedure affords the target compounds in high yields and diastereoselectivities.

SUBMITTER: Martin RM

PROVIDER: S-EPMC3570756 | biostudies-literature | 2013 Feb

REPOSITORIES: biostudies-literature

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Synthesis of isoquinuclidines from highly substituted dihydropyridines via the Diels-Alder reaction.

Martin Rhia M RM Bergman Robert G RG Ellman Jonathan A JA

Organic letters 20130115 3

A stereo- and regioselective Diels-Alder reaction for the synthesis of highly substituted isoquinuclidines from dihydropyridines and electron-deficient alkenes has been developed. While reactions with activated dienophiles proceed readily under thermal conditions, the use of Lewis acid additives is necessary to facilitate cycloadditions for less reactive alkenes. This procedure affords the target compounds in high yields and diastereoselectivities. ...[more]

PMID: 23320852

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