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Organocatalytic Asymmetric Friedel—Crafts Alkylation/Cyclization Cascade Reaction of 1-Napthols and α,β,-Unsaturated Aldehydes: An Enantioselective Synthesis of Chromanes and Dihydrobenzopyranes.
- Source :
-
Journal of Organic Chemistry . 9/4/2009, Vol. 74 Issue 17, p6881-6884. 4p. 2 Charts. - Publication Year :
- 2009
-
Abstract
- An enantioselective Fnedel—Crafts alkylation/cyclization cascade reaction of l-naphthols and α,β-unsaturated aIdehydes promoted by diphenylprolinol ether has been developed. The method affords one-pot access to chiral and synthetically useful chromanes and dihydrobenzopyranes in high yields and enantioselectivities from readily available compounds. In addition, the addition/cyclization products could be afterward transformed to various natural products and biologically active derivatives. On the basis of the experimental results and the observed absolute configurations of the products, a plausible mechanism has been proposed to explain the origin of the activation and the asymmetric induction. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 74
- Issue :
- 17
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 44221687
- Full Text :
- https://doi.org/10.1021/jo901409d