Literature DB >> 26058560

Gadolinium-Catalyzed Regio- and Enantioselective Aminolysis of Aromatic trans-2,3-Epoxy Sulfonamides.

Chuan Wang1, Hisashi Yamamoto2,3.   

Abstract

The first enantioselective aminolysis of aromatic trans-2,3-epoxy sulfonamides has been accomplished, which was efficiently catalyzed by a Gd-N,N'-dioxide complex. Under the directing effect of the sulfonamide moiety the ring-opening reaction proceeded selectively at the C-3 position in a highly enantioselective manner furnishing various Ts- and SES-protected 3-amino-3-phenylpropan-2-olamines as products.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  amino alcohols; gadolinium-catalysis; kinetic resolution; regioselective; ring opening

Mesh：

Substances：

Year:  2015        PMID： 26058560      PMCID： PMC4526255          DOI： 10.1002/anie.201503391

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  14 in total

1.  Asymmetric catalysis with water: efficient kinetic resolution of terminal epoxides by means of catalytic hydrolysis.

Authors:  M Tokunaga; J F Larrow; F Kakiuchi; E N Jacobsen
Journal:  Science       Date:  1997-08-15       Impact factor: 47.728

2.  N,N'-Dioxide/Gadolinium(III)-Catalyzed Asymmetric Conjugate Addition of Nitroalkanes to α,β-Unsaturated Pyrazolamides.

Authors:  Qian Yao; Zhen Wang; Yuheng Zhang; Xiaohua Liu; Lili Lin; Xiaoming Feng
Journal:  J Org Chem       Date:  2015-05-13       Impact factor: 4.354

3.  A broadly applicable and practical oligomeric (salen) Co catalyst for enantioselective epoxide ring-opening reactions.

Authors:  David E White; Pamela M Tadross; Zhe Lu; Eric N Jacobsen
Journal:  Tetrahedron       Date:  2014-07-08       Impact factor: 2.457

4.  Tungsten-, molybdenum-, and cerium-promoted regioselective and stereospecific halogenation of 2,3-epoxy alcohols and 2,3-epoxy sulfonamides.

Authors:  Chuan Wang; Hisashi Yamamoto
Journal:  Org Lett       Date:  2014-11-10       Impact factor: 6.005

5.  Nickel-catalyzed regio- and enantioselective aminolysis of 3,4-epoxy alcohols.

Authors:  Chuan Wang; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2015-03-25       Impact factor: 15.419

6.  Tungsten-catalyzed regio- and enantioselective aminolysis of trans-2,3-epoxy alcohols: an entry to virtually enantiopure amino alcohols.

Authors:  Chuan Wang; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-19       Impact factor: 15.336

7.  1-(Indolin-1-yl)-1-phenyl-3-propan-2-olamines as potent and selective norepinephrine reuptake inhibitors.

Authors:  An T Vu; Stephen T Cohn; Puwen Zhang; Callain Y Kim; Paige E Mahaney; Jenifer A Bray; Grace H Johnston; Elizabeth J Koury; Scott A Cosmi; Darlene C Deecher; Valerie A Smith; James E Harrison; Liza Leventhal; Garth T Whiteside; Jeffrey D Kennedy; Eugene J Trybulski
Journal:  J Med Chem       Date:  2010-03-11       Impact factor: 7.446

8.  3-(Arylamino)-3-phenylpropan-2-olamines as a new series of dual norepinephrine and serotonin reuptake inhibitors.

Authors:  An T Vu; Stephen T Cohn; Eugene A Terefenko; William J Moore; Puwen Zhang; Paige E Mahaney; Eugene J Trybulski; Igor Goljer; Rebecca Dooley; Jenifer A Bray; Grace H Johnston; Jennifer Leiter; Darlene C Deecher
Journal:  Bioorg Med Chem Lett       Date:  2009-03-18       Impact factor: 2.823

9.  Kinetic resolution of epoxides by a C-C bond-forming reaction: highly enantioselective addition of indoles to cis, trans, and meso aromatic epoxides catalyzed by [Cr(salen)] complexes.

Authors:  Marco Bandini; Pier Giorgio Cozzi; Paolo Melchiorre; Achille Umani-Ronchi
Journal:  Angew Chem Int Ed Engl       Date:  2004-01       Impact factor: 15.336

10.  Tungsten-catalyzed regioselective and stereospecific ring opening of 2,3-epoxy alcohols and 2,3-epoxy sulfonamides.

Authors:  Chuan Wang; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2014-05-02       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.