Literature DB >> 21410270

Asymmetric Synthesis of 1,3-Diamines. II: Diastereoselective reduction of atropisomeric N-tert-butanesulfinylketimines.

Marina Martjuga1, Sergey Belyakov, Edvards Liepinsh, Edgars Suna.   

Abstract

Chiral, nonracemic o-aminobenzylamines were prepared in a highly diastereoselective reduction of atropisomeric N-tert-butanesulfinylketimines. The ortho-substituent ensures the distinct reactivity of atropisomers 4d-f. The free energy of activation for atropisomerization of sulfinylimines 4d-f in THF-d(8) was determined by NMR methods to range from 70.8 to 97.9 kJ/mol.

Entities:  

Year:  2011        PMID: 21410270     DOI: 10.1021/jo1025767

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


  5 in total

1.  1,4-Diazaspiro[2.2]pentanes as a flexible platform for the synthesis of diamine-bearing stereotriads.

Authors:  Jared W Rigoli; Luke A Boralsky; John C Hershberger; Dagmara Marston; Alan R Meis; Ilia A Guzei; Jennifer M Schomaker
Journal:  J Org Chem       Date:  2012-02-14       Impact factor: 4.354

2.  Synthesis of 1,3-diaminated stereotriads via rearrangement of 1,4-diazaspiro[2.2]pentanes.

Authors:  Cale D Weatherly; Jared W Rigoli; Jennifer M Schomaker
Journal:  Org Lett       Date:  2012-03-20       Impact factor: 6.005

3.  A novel asymmetric synthesis of cinacalcet hydrochloride.

Authors:  Veera R Arava; Laxminarasimhulu Gorentla; Pramod K Dubey
Journal:  Beilstein J Org Chem       Date:  2012-08-24       Impact factor: 2.883

4.  Pd(OAc)2-catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines.

Authors:  Jianzhong Chen; Zhenfeng Zhang; Bowen Li; Feilong Li; Yulin Wang; Min Zhao; Ilya D Gridnev; Tsuneo Imamoto; Wanbin Zhang
Journal:  Nat Commun       Date:  2018-11-27       Impact factor: 14.919

5.  Synthetic Approach toward Enantiopure Cyclic Sulfinamides.

Authors:  Glebs Jersovs; Matiss Bojars; Pavel A Donets; Edgars Suna
Journal:  Org Lett       Date:  2022-06-16       Impact factor: 6.072

  5 in total

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