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Asymmetric Conjugate Reductions of Coumarins. A New Route to Tolterodine and Related Coumarin Derivatives
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Abstract
The combination of catalytic amounts of [(R)-DTBM-SEGPHOS]CuH in the presence of stoichiometric DEMS (diethoxymethylsilane) in toluene at room temperature leads to asymmetric reductions of 4-substituted coumarins. Several targets or their known precursors can be prepared in high yields and ee’s, including the muscarine receptor antagonist (R)-tolterodine.
Citing Articles
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This article has been cited by 4 ACS Journal articles (4 most recent appear below).
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Xiang Wang, Anil Guram, Seb Caille, Jack Hu, J P. Preston, Michael Ronk, and Shawn WalkerOrganic Letters2011 13 (7), 1881-1883A new synthetic strategy that turns styrene-type olefins into excellent substrates for Rh-catalyzed asymmetric hydrogenation by installing a 2′-hydroxyl substituent is described. This methodology accommodates trisubstituted olefinic substrates in various ...
Stereoselective Synthesis of Unsymmetrical β,β-Diarylacrylates by a Heck−Matsuda Reaction: Versatile Building Blocks for Asymmetric Synthesis of β,β-Diphenylpropanoates, 3-Aryl-indole, and 4-Aryl-3,4-dihydro-quinolin-2-one and Formal Synthesis of (−)-Indatraline
Jason G. Taylor and Carlos Roque D. CorreiaThe Journal of Organic Chemistry2011 76 (3), 857-869Stereoselective Synthesis of Unsymmetrical β,β-Diarylacrylates by a Heck−Matsuda Reaction: Versatile Building Blocks for Asymmetric Synthesis of β,β-Diphenylpropanoates, 3-Aryl-indole, and 4-Aryl-3,4-dihydro-quinolin-2-one and Formal Synthesis of (−)-Indatraline
Jason G. Taylor and Carlos Roque D. CorreiaThe Journal of Organic Chemistry2011 76 (3), 857-869β,β-Disubstituted α,β-unsaturated esters may serve as valuable derivatives for the preparation of other highly functionalized systems found in many natural products and marketed drugs. The stereoselective synthesis of unsymmetrical β,β-diarylacrylate ...
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History
- Published In Issue December 03, 2009
- Article ASAPOctober 30, 2009
- Received: September 2, 2009
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