Literature DB >> 19877705

Asymmetric conjugate reductions of coumarins. A new route to tolterodine and related coumarin derivatives.

Brian D Gallagher1, Benjamin R Taft, Bruce H Lipshutz.   

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.

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Year:  2009        PMID: 19877705     DOI: 10.1021/ol9020404

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  9 in total

1.  N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.

Authors:  Anna Lee; Karl A Scheidt
Journal:  Chem Commun (Camb)       Date:  2015-02-25       Impact factor: 6.222

2.  CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes.

Authors:  Yujing Zhou; Jeffrey S Bandar; Richard Y Liu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2018-01-04       Impact factor: 15.419

3.  A new strategy for the synthesis of chiral β-alkynyl esters via sequential palladium and copper catalysis.

Authors:  Barry M Trost; Benjamin R Taft; James T Masters; Jean-Philip Lumb
Journal:  J Am Chem Soc       Date:  2011-05-16       Impact factor: 15.419

4.  A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with Terminal Allenes.

Authors:  Erica Y Tsai; Richard Y Liu; Yang Yang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2018-02-02       Impact factor: 15.419

5.  Enantioselective synthesis of (R)-tolterodine using lithiation/borylation-protodeboronation methodology.

Authors:  Stefan Roesner; Varinder K Aggarwal
Journal:  Can J Chem       Date:  2012-11       Impact factor: 1.118

6.  On the Absolute Stereochemistry of Tolterodine: A Circular Dichroism Study.

Authors:  Marcin Górecki; Valerio Zullo; Anna Iuliano; Gennaro Pescitelli
Journal:  Pharmaceuticals (Basel)       Date:  2019-01-26

7.  Efficient kinetic resolution in the asymmetric transfer hydrogenation of 3-aryl-indanones: applications to a short synthesis of (+)-indatraline and a formal synthesis of (R)-tolterodine.

Authors:  Songsoon Park; Hyeon-Kyu Lee
Journal:  RSC Adv       Date:  2021-06-30       Impact factor: 3.361

8.  Chiral Fe(ii) complex catalyzed enantioselective [1,3] O-to-C rearrangement of alkyl vinyl ethers and synthesis of chromanols and beyond.

Authors:  Lifeng Wang; Pengfei Zhou; Qianchi Lin; Shunxi Dong; Xiaohua Liu; Xiaoming Feng
Journal:  Chem Sci       Date:  2020-09-07       Impact factor: 9.825

Review 9.  Recent Advances in Synthesis of 4-Arylcoumarins.

Authors:  Jong-Wha Jung; Nam-Jung Kim; Hwayoung Yun; Young Taek Han
Journal:  Molecules       Date:  2018-09-20       Impact factor: 4.411

  9 in total

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