Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 17, Pages 6881-6884Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo901409d
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Funding
- NSFC [20525206, 20772052, 90813012, 20621091]
- Chang Jiang Scholar Program of the Ministry of Education of China
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An enantioselective Friedel-Crafts alkylation/cyclization cascade reaction of 1-naphthols and alpha,beta-unsaturated aldehydes promoted by diphenylprolinol ether has been developed. The method affords one-pot access to chiral and synthetically useful chromanes and dihydrobenzopyranes ill 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.
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