Literature DB >> 16930038

Reversal of diastereofacial selectivity in hydride reductions of N-tert-butanesulfinyl imines.

John T Colyer1, Neil G Andersen, Jason S Tedrow, Troy S Soukup, Margaret M Faul.   

Abstract

A variety of N-tert-butanesulfinyl imines were reduced with NaBH4 in THF containing 2% water to provide the corresponding secondary sulfinamides in high yield and diastereoselectivity. By using the same sulfinyl imine starting materials and changing the reductant to L-Selectride, the stereoselectivity could be efficiently reversed to afford the opposite product diastereomer in high yield and selectivity.

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Year:  2006        PMID: 16930038     DOI: 10.1021/jo0609834

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  13 in total

1.  Asymmetric synthesis and in vitro and in vivo activity of tetrahydroquinolines featuring a diverse set of polar substitutions at the 6 position as mixed-efficacy μ opioid receptor/δ opioid receptor ligands.

Authors:  Aaron M Bender; Nicholas W Griggs; Jessica P Anand; John R Traynor; Emily M Jutkiewicz; Henry I Mosberg
Journal:  ACS Chem Neurosci       Date:  2015-05-13       Impact factor: 4.418

2.  Discovery of Potent 2-Aryl-6,7-dihydro-5 H-pyrrolo[1,2- a]imidazoles as WDR5-WIN-Site Inhibitors Using Fragment-Based Methods and Structure-Based Design.

Authors:  Feng Wang; Kyu Ok Jeon; James M Salovich; Jonathan D Macdonald; Joseph Alvarado; Rocco D Gogliotti; Jason Phan; Edward T Olejniczak; Qi Sun; Shidong Wang; DeMarco Camper; Joannes P Yuh; J Grace Shaw; Jiqing Sai; Olivia W Rossanese; William P Tansey; Shaun R Stauffer; Stephen W Fesik
Journal:  J Med Chem       Date:  2018-06-29       Impact factor: 7.446

3.  Effects of N-Substitutions on the Tetrahydroquinoline (THQ) Core of Mixed-Efficacy μ-Opioid Receptor (MOR)/δ-Opioid Receptor (DOR) Ligands.

Authors:  Aubrie A Harland; Aaron M Bender; Nicholas W Griggs; Chao Gao; Jessica P Anand; Irina D Pogozheva; John R Traynor; Emily M Jutkiewicz; Henry I Mosberg
Journal:  J Med Chem       Date:  2016-05-16       Impact factor: 7.446

4.  Design, synthesis, and X-ray studies of potent HIV-1 protease inhibitors incorporating aminothiochromane and aminotetrahydronaphthalene carboxamide derivatives as the P2 ligands.

Authors:  Arun K Ghosh; Ravindra D Jadhav; Hannah Simpson; Satish Kovela; Heather Osswald; Johnson Agniswamy; Yuan-Fang Wang; Shin-Ichiro Hattori; Irene T Weber; Hiroaki Mitsuya
Journal:  Eur J Med Chem       Date:  2018-09-18       Impact factor: 6.514

5.  Further Optimization and Evaluation of Bioavailable, Mixed-Efficacy μ-Opioid Receptor (MOR) Agonists/δ-Opioid Receptor (DOR) Antagonists: Balancing MOR and DOR Affinities.

Authors:  Aubrie A Harland; Larisa Yeomans; Nicholas W Griggs; Jessica P Anand; Irina D Pogozheva; Emily M Jutkiewicz; John R Traynor; Henry I Mosberg
Journal:  J Med Chem       Date:  2015-11-13       Impact factor: 7.446

6.  Placement of Hydroxy Moiety on Pendant of Peptidomimetic Scaffold Modulates Mu and Kappa Opioid Receptor Efficacy.

Authors:  Aubrie A Harland; Irina D Pogozheva; Nicholas W Griggs; Tyler J Trask; John R Traynor; Henry I Mosberg
Journal:  ACS Chem Neurosci       Date:  2017-08-25       Impact factor: 4.418

7.  A general and simple diastereoselective reduction by L-Selectride: efficient synthesis of protected (4S,5S)-dihydroxy amides.

Authors:  Bo Yin; Dong-Nai Ye; Kai-Hui Yu; Liang-Xian Liu
Journal:  Molecules       Date:  2010-04-16       Impact factor: 4.411

8.  Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction.

Authors:  Yiwen Xiong; Haibo Mei; Lingmin Wu; Jianlin Han; Yi Pan; Guigen Li
Journal:  Beilstein J Org Chem       Date:  2014-03-13       Impact factor: 2.883

9.  From racemic alcohols to enantiopure amines: Ru-catalyzed diastereoselective amination.

Authors:  Nathan J Oldenhuis; Vy M Dong; Zhibin Guan
Journal:  J Am Chem Soc       Date:  2014-08-29       Impact factor: 15.419

Review 10.  N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles.

Authors:  Joseane A Mendes; Paulo R R Costa; Miguel Yus; Francisco Foubelo; Camilla D Buarque
Journal:  Beilstein J Org Chem       Date:  2021-05-12       Impact factor: 2.883

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