Literature DB >> 16636728

Catalytic asymmetric approaches towards enantiomerically enriched diarylmethanols and diarylmethylamines.

Frank Schmidt1, René T Stemmler, Jens Rudolph, Carsten Bolm.   

Abstract

Enantiopure diarylmethanols and diarylmethylamines are important intermediates for the synthesis of pharmaceutically relevant products with antihistaminic, antiarrhythmic, diuretic, antidepressive, laxative, local-anesthetic and anticholinergic properties. Furthermore, they have been used as precursors for 1,1-diarylalkyl moieties, which occur in other antidepressants as well as in antimuscarinics and endothelin antagonists. In this critical review catalytic strategies towards enantioenriched diarylmethanols and diarylmethylamines are discussed, including methods for asymmetric carbon-carbon bond formations by aryl transfer reactions to aldehydes and arylimines, respectively, and enantioselective reductions of diarylketones.

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Year:  2006        PMID: 16636728     DOI: 10.1039/b600091f

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  32 in total

1.  Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.

Authors:  Minyan Li; Baris Yücel; Javier Adrio; Ana Bellomo; Patrick J Walsh
Journal:  Chem Sci       Date:  2014-06-01       Impact factor: 9.825

2.  Diastereoselective chelation-controlled additions to β-silyloxy aldehydes.

Authors:  Gretchen R Stanton; Meara C Kauffman; Patrick J Walsh
Journal:  Org Lett       Date:  2012-06-21       Impact factor: 6.005

3.  Combined Photoredox/Enzymatic C-H Benzylic Hydroxylations.

Authors:  Rick C Betori; Catherine M May; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-26       Impact factor: 15.336

4.  A Chiral Nitrogen Ligand for Enantioselective, Iridium-Catalyzed Silylation of Aromatic C-H Bonds.

Authors:  Bo Su; Tai-Gang Zhou; Xian-Wei Li; Xiao-Ru Shao; Pei-Lin Xu; Wen-Lian Wu; John F Hartwig; Zhang-Jie Shi
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-15       Impact factor: 15.336

5.  Room-temperature enantioselective C-H iodination via kinetic resolution.

Authors:  Ling Chu; Kai-Jiong Xiao; Jin-Quan Yu
Journal:  Science       Date:  2014-10-24       Impact factor: 47.728

6.  Rhodium-catalyzed enantioselective silylation of arene C-H bonds: desymmetrization of diarylmethanols.

Authors:  Taegyo Lee; Tyler W Wilson; Robert Berg; Per Ryberg; John F Hartwig
Journal:  J Am Chem Soc       Date:  2015-05-20       Impact factor: 15.419

7.  Formation of C-C Bonds via Iridium-Catalyzed Hydrogenation and Transfer Hydrogenation.

Authors:  John F Bower; Michael J Krische
Journal:  Top Organomet Chem       Date:  2011-01-01       Impact factor: 1.311

8.  Continuous flow enantioselective arylation of aldehydes with ArZnEt using triarylboroxins as the ultimate source of aryl groups.

Authors:  Julien Rolland; Xacobe C Cambeiro; Carles Rodríguez-Escrich; Miquel A Pericàs
Journal:  Beilstein J Org Chem       Date:  2009-10-15       Impact factor: 2.883

9.  Nickel-catalyzed asymmetric cross-couplings of racemic propargylic halides with arylzinc reagents.

Authors:  Sean W Smith; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2008-09-03       Impact factor: 15.419

10.  Enantioselective Copper(I)-Catalyzed Alkynylation of Oxocarbenium Ions to Set Diaryl Tetrasubstituted Stereocenters.

Authors:  Srimoyee Dasgupta; Thomas Rivas; Mary P Watson
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-25       Impact factor: 15.336

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