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Org Lett. 2013 Feb 1;15(3):444-7. doi: 10.1021/ol303040r. Epub 2013 Jan 15.

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

Author information

1
Department of Chemistry, Yale University, New Haven, Connecticut 06520, USA.

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.

PMID:
23320852
PMCID:
PMC3570756
DOI:
10.1021/ol303040r
[Indexed for MEDLINE]
Free PMC Article

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