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Synfacts 2009(11): 1181-1181
DOI: 10.1055/s-0029-1218036
DOI: 10.1055/s-0029-1218036
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of (R)-Tolterodine
Contributor(s):Philip KocienskiK. Yoo, H. Kim, J. Yun*
Sungkyunkwan University, Suwon, Korea
Enantioselective Synthesis of (R)-Tolterodine via CuH-Catalyzed Asymmetric Conjugate Reduction
J. Org. Chem. 2009, 74: 4232-4235
Sungkyunkwan University, Suwon, Korea
Enantioselective Synthesis of (R)-Tolterodine via CuH-Catalyzed Asymmetric Conjugate Reduction
J. Org. Chem. 2009, 74: 4232-4235
Further Information
Publication History
Publication Date:
22 October 2009 (online)
Key words
tolterodine - hydroarylation - asymmetric conjugate reduction - boronic acids - copper
Significance
(R)-Tolterodine is a muscarinic antagonist used for the treatment of urinary incontinence. Key steps in the short synthesis depicted are (1) a copper-catalyzed addition (hydroarylation) of phenylboronic acid to an alkynylnitrile (C → D) and (2) a CuH-catalyzed asymmetric conjugate reduction of an α,β-unsaturated nitrile (D → E).
Comment
Copper-catalyzed hydroarylation of alkynoates had been reported previously by Y. Yamamoto, N. Kirai and Y. Harada (Chem. Commun. 2008, 2010).
Review: CuH-Catalyzed Reactions, C. Deutsch, N. Krause, B. C. Lipshutz, Chem. Rev. 2008, 108, 2916-2927.