Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins: asymmetric synthesis of (R)-tolterodine

Gang Chen; Norihito Tokunaga; Tamio Hayashi

doi:10.1021/ol0507367

Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins: asymmetric synthesis of (R)-tolterodine

Org Lett. 2005 May 26;7(11):2285-8. doi: 10.1021/ol0507367.

Authors

Gang Chen¹, Norihito Tokunaga, Tamio Hayashi

Affiliation

¹ Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.

PMID: 15901190
DOI: 10.1021/ol0507367

Abstract

[reaction: see text]. Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins proceeded with high enantioselectivity in the presence of a rhodium catalyst (3 mol %) generated from Rh(acac)(C2H4)2 and (R)-Segphos to give the corresponding (R)-4-arylchroman-2-ones in over 99% ee. This asymmetric reaction was applied to the synthesis of (R)-tolterodine.

Publication types

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

MeSH terms

Benzhydryl Compounds / analysis
Benzhydryl Compounds / chemical synthesis*
Boronic Acids / chemistry*
Catalysis
Coumarins / chemistry*
Cresols / analysis
Cresols / chemical synthesis*
Molecular Structure
Phenylpropanolamine / analysis
Phenylpropanolamine / chemical synthesis*
Rhodium / chemistry*
Stereoisomerism
Tolterodine Tartrate

Substances

Benzhydryl Compounds
Boronic Acids
Coumarins
Cresols
Phenylpropanolamine
Tolterodine Tartrate
Rhodium