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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.OL

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.

Authors+Show Affiliations

Chen G
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.
Tokunaga N
No affiliation info available
Hayashi T
No affiliation info available

MeSH

Benzhydryl CompoundsBoronic AcidsCatalysisCoumarinsCresolsMolecular StructurePhenylpropanolamineRhodiumStereoisomerismTolterodine Tartrate

Pub Type(s)

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

Language

eng

PubMed ID

15901190

Citation

Chen, Gang, et al. "Rhodium-catalyzed Asymmetric 1,4-addition of Arylboronic Acids to Coumarins: Asymmetric Synthesis of (R)-tolterodine." Organic Letters, vol. 7, no. 11, 2005, pp. 2285-8.
Chen G, Tokunaga N, Hayashi T. Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins: asymmetric synthesis of (R)-tolterodine. Org Lett. 2005;7(11):2285-8.
Chen, G., Tokunaga, N., & Hayashi, T. (2005). Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins: asymmetric synthesis of (R)-tolterodine. Organic Letters, 7(11), 2285-8.
Chen G, Tokunaga N, Hayashi T. 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. PubMed PMID: 15901190.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins: asymmetric synthesis of (R)-tolterodine. AU - Chen,Gang, AU - Tokunaga,Norihito, AU - Hayashi,Tamio, PY - 2005/5/20/pubmed PY - 2006/2/28/medline PY - 2005/5/20/entrez SP - 2285 EP - 8 JF - Organic letters JO - Org Lett VL - 7 IS - 11 N2 - [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. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/15901190/Rhodium_catalyzed_asymmetric_14_addition_of_arylboronic_acids_to_coumarins:_asymmetric_synthesis_of__R__tolterodine_ DB - PRIME DP - Unbound Medicine ER -