Enantioselective Friedel-Crafts reaction of beta-trifluoromethylated acrylates with pyrroles and its application to the synthesis of trifluorinated heliotridane

Yiyong Huang; Etsuko Tokunaga; Satoru Suzuki; Motoo Shiro; Norio Shibata

doi:10.1021/ol100171z

Enantioselective Friedel-Crafts reaction of beta-trifluoromethylated acrylates with pyrroles and its application to the synthesis of trifluorinated heliotridane

Org Lett. 2010 Mar 5;12(5):1136-8. doi: 10.1021/ol100171z.

Authors

Yiyong Huang¹, Etsuko Tokunaga, Satoru Suzuki, Motoo Shiro, Norio Shibata

Affiliation

¹ Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.

PMID: 20143845
DOI: 10.1021/ol100171z

Abstract

The first chiral Lewis acid catalyzed enantioselective Friedel-Crafts alkylation of pyrroles with beta-CF(3) acrylates has been investigated, which afforded various types of chiral trifluoromethylated compounds in excellent yields (90-99%) with high ee's (up to 99% ee). With the aid of the Friedel-Crafts reaction adduct, optically active trifluorinated heliotridane was successfully constructed.

Publication types

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

MeSH terms

Acrylates / chemistry*
Pyrroles / chemistry*
Pyrrolizidine Alkaloids / chemical synthesis*
Pyrrolizidine Alkaloids / chemistry*
Stereoisomerism
Substrate Specificity

Substances

Acrylates
Pyrroles
Pyrrolizidine Alkaloids
heliotridane