Diastereoselective synthesis of 6-trifluoromethyl-5,6-dihydropyrans via phosphine-catalyzed [4 + 2] annulation of α-benzylallenoates with ketones

Tong Wang; Song Ye

doi:10.1021/ol101762z

Diastereoselective synthesis of 6-trifluoromethyl-5,6-dihydropyrans via phosphine-catalyzed [4 + 2] annulation of α-benzylallenoates with ketones

Org Lett. 2010 Sep 17;12(18):4168-71. doi: 10.1021/ol101762z.

Authors

Tong Wang¹, Song Ye

Affiliation

¹ Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.

PMID: 20712333
DOI: 10.1021/ol101762z

Abstract

The highly diastereoselective synthesis of 6-trifluoromethyl-5,6-dihydropyrans was realized by the phosphine-catalyzed [4 + 2] annulation of ethyl α-benzylallenoates and trifluoromethyl ketones.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzyl Compounds / chemistry*
Catalysis
Crystallography, X-Ray
Fluorine Compounds / chemistry*
Hydroxylation
Ketones / chemistry*
Methylation
Models, Molecular
Molecular Structure
Naphthalenes / chemistry*
Phosphines / chemistry*
Stereoisomerism

Substances

Benzyl Compounds
Fluorine Compounds
Ketones
Naphthalenes
Phosphines
phosphine
allenolic acid