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- Title
Asymmetric Organocatalytic Benzylation of α,β-Unsaturated Aldehydes with Toluenes.
- Authors
Dell'Amico, Luca; Companyó, Xavier; Naicker, Tricia; Bräuer, Thomas M.; Jørgensen, Karl Anker
- Abstract
The direct organocatalytic enantioselective benzylation by using toluenes and α,β-unsaturated aldehydes is presented. The reaction is catalyzed by tert-butyldimethylsilyl-protected diphenylprolinol in the presence of a mild organic base and proceeds with excellent yields and enantioselectivities up to >99 % ee. This reactivity is based on a synergistic effect between the iminium ion intermediate and the base-activated toluene. Toluene derivatives having various electron-withdrawing substituents were also applied in this unprecedented transformation. The synthetic potential is demonstrated by manipulations of the products to, for example, biologically active phenylbenzazepines.
- Subjects
AROMATIC compounds; TOLUENE; ORGANIC compounds; ORGANIC chemistry; PARTICLES (Nuclear physics)
- Publication
European Journal of Organic Chemistry, 2013, Vol 2013, Issue 24, p5262
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201300899