exo-Selective asymmetric Diels-Alder reaction catalyzed by diamine salts as organocatalysts.

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Abstract

An organocatalyst formed from a binaphthyl-substituted diamine and trifluoromethanesulfonic acid exhibited unprecedented levels of exo selectivity in the Diels-Alder reaction of alpha,beta-unsaturated aldehydes with cyclopentadiene. A novel axially chiral diamine was also designed as an organocatalyst for an asymmetric variant of this reaction, in which the desired cycloadducts were formed with high diastereo- and enantioselectivities. The highest diastereoselectivity observed was greater than 20:1 in favor of the exo cycloadduct in the asymmetric Diels-Alder reaction of crotonaldehyde with cyclopentadiene.

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Journal

Journal ID (iso-abbrev): Chem Asian J

Title: Chemistry, an Asian journal

Publisher: Wiley-Blackwell

ISSN (Electronic): 1861-471X

ISSN (Print): 1861-471X

Publication date (Electronic): Sep 03 2007

Volume: 2

Issue: 9

Affiliations

[1 ] Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.

Article

DOI: 10.1002/asia.200700122

PubMed ID: 17640000

SO-VID: 8c15dd6e-eff6-4dac-b3ea-e80d670bb9ac

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