Literature DB >> 16597143

Stereoselective nucleophilic monofluoromethylation of N-(tert-butanesulfinyl)imines with fluoromethyl phenyl sulfone.

Ya Li1, Chuanfa Ni, Jun Liu, Laijun Zhang, Ji Zheng, Lingui Zhu, Jinbo Hu.   

Abstract

[reaction: see text] Highly stereoselective nucleophilic monofluoromethylation of (R)-(tert-butanesulfinyl)imines with fluoromethyl phenyl sulfone was achieved to afford alpha-monofluoromethylamines with a nonchelation-controlled stereoselectivity mode. By using the same chemistry, (R)-(tert-butanesulfinyl)imines bearing a terminal tosylate (OTs) group can be converted to alpha-monofluoromethylated cyclic secondary amines with high stereoselectivity.

Entities:  

Year:  2006        PMID： 16597143     DOI： 10.1021/ol060322t

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


  5 in total

1.  Stereoselective synthesis of cis-2,5-disubstituted pyrrolidines via Wacker-type aerobic oxidative cyclization of alkenes with tert-butanesulfinamide nucleophiles.

Authors:  Joanne E Redford; Richard I McDonald; Matthew L Rigsby; Joshua D Wiensch; Shannon S Stahl
Journal:  Org Lett       Date:  2012-02-21       Impact factor: 6.005

2.  Catalytic enantioselective synthesis of fluoromethylated stereocenters by asymmetric hydrogenation.

Authors:  Jianping Yang; Sudipta Ponra; Xingzhen Li; Bram B C Peters; Luca Massaro; Taigang Zhou; Pher G Andersson
Journal:  Chem Sci       Date:  2022-06-29       Impact factor: 9.969

3.  Practical and innate carbon-hydrogen functionalization of heterocycles.

Authors:  Yuta Fujiwara; Janice A Dixon; Fionn O'Hara; Erik Daa Funder; Darryl D Dixon; Rodrigo A Rodriguez; Ryan D Baxter; Bart Herlé; Neal Sach; Michael R Collins; Yoshihiro Ishihara; Phil S Baran
Journal:  Nature       Date:  2012-11-28       Impact factor: 49.962

4.  Enantioselective nucleophilic difluoromethylation of aromatic aldehydes with Me3SiCF2SO2Ph and PhSO2CF2H reagents catalyzed by chiral quaternary ammonium salts.

Authors:  Chuanfa Ni; Fang Wang; Jinbo Hu
Journal:  Beilstein J Org Chem       Date:  2008-06-26       Impact factor: 2.883

5.  Crystal structure of 1-fluoro-1,3-di-hydro-benzo[c]thio-phene 2,2-dioxide.

Authors:  Ying Zou; Zibin Qiu; Renming Tang; Kaixu Yuan; Ya Li
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-09-12
  5 in total

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