Literature DB >> 15816732

A room-temperature protocol for the rhodium(I)-catalyzed addition of arylboron compounds to sulfinimines.

Yuri Bolshan1, Robert A Batey.   

Abstract

[reaction: see text] The addition of organoboronic acids to chiral sulfinimines proceeds under mild conditions at room temperature, using Rh(I) catalysis in the absence of external phosphine ligands. Clean reaction only occurs in the presence of water as a cosolvent. The sulfinamide adducts are formed with high diastereoselectivities, providing a convenient route to the synthesis of enantiomerically enriched chiral benzylic amines.

Entities:  

Year:  2005        PMID: 15816732     DOI: 10.1021/ol050014f

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


  6 in total

1.  Highly diastereoselective and general synthesis of primary β-fluoroamines.

Authors:  Michael L Schulte; Craig W Lindsley
Journal:  Org Lett       Date:  2011-09-26       Impact factor: 6.005

2.  SYNTHESIS OF DE NOVO CHIRAL γ-AMINO-YNAMIDES USING LITHIATED YNAMIDES. OBSERVATION OF A UNIQUE 5-ENDO-DIG CYCLIZATION WITH AN INVERSION OF S-CENTER.

Authors:  Xiao-Na Wang; Richard P Hsung; Sierra K Fox; Ming-Can Lv; Rui Qi
Journal:  Heterocycles       Date:  2014-01-01       Impact factor: 0.831

3.  Asymmetric synthesis of amines using tert-butanesulfinamide.

Authors:  Hai-Chao Xu; Somenath Chowdhury; Jonathan A Ellman
Journal:  Nat Protoc       Date:  2013-10-24       Impact factor: 13.491

4.  Enantioselective addition of boronates to acyl imines catalyzed by chiral biphenols.

Authors:  Joshua A Bishop; Sha Lou; Scott E Schaus
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

5.  Enantioselective ortho-C-H cross-coupling of diarylmethylamines with organoborons.

Authors:  Brian N Laforteza; Kelvin S L Chan; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-04       Impact factor: 15.336

6.  Phosphinite- and phosphite-based Type I palladacycles as highly active catalysts for addition reactions of arylboronic acids with aldehydes, α,β-unsaturated ketones, α-ketoesters, and aldimines.

Authors:  Ping He; Yong Lu; Qiao-Sheng Hu
Journal:  Tetrahedron Lett       Date:  2007-07-23       Impact factor: 2.415

  6 in total

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