Literature DB >> 16045335

Ni(II) Tol-BINAP-catalyzed enantioselective orthoester alkylations of N-acylthiazolidinethiones.

David A Evans1, Regan J Thomson.   

Abstract

The development of a Ni(II) (S)-Tol-BINAP-catalyzed enantioselective alkylation of N-acylthiazolidinethiones with trimethyl orthoformate is described. The reaction is general with respect to the thiazolidinethione, providing the desired adducts in good to excellent yield and with high levels of enantioselectivity (11 examples, 51-92% yield, 90-99% ee). The products are readily converted into a variety of synthetically useful derivatives in a straightforward manner.

Entities:  

Mesh:

Substances:

Year:  2005        PMID: 16045335     DOI: 10.1021/ja053386s

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  10 in total

1.  Copper-Catalyzed Aminothiolation of 1,3-Dienes via a Dihydrothiazine Intermediate.

Authors:  Christopher E Sleet; Uttam K Tambar
Journal:  Angew Chem Int Ed Engl       Date:  2017-04-13       Impact factor: 15.336

2.  A highly enantioselective intramolecular Michael reaction catalyzed by N-heterocyclic carbenes.

Authors:  Eric M Phillips; Manabu Wadamoto; Audrey Chan; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  Enantioselective copper-catalyzed alkynylation of benzopyranyl oxocarbenium ions.

Authors:  Harathi D Srinivas; Prantik Maity; Glenn P A Yap; Mary P Watson
Journal:  J Org Chem       Date:  2015-04-07       Impact factor: 4.354

4.  Copper-catalyzed enantioselective additions to oxocarbenium ions: alkynylation of isochroman acetals.

Authors:  Prantik Maity; Harathi D Srinivas; Mary P Watson
Journal:  J Am Chem Soc       Date:  2011-10-11       Impact factor: 15.419

5.  A systematic investigation of quaternary ammonium ions as asymmetric phase-transfer catalysts. Synthesis of catalyst libraries and evaluation of catalyst activity.

Authors:  Scott E Denmark; Nathan D Gould; Larry M Wolf
Journal:  J Org Chem       Date:  2011-05-06       Impact factor: 4.354

6.  NHC-catalyzed reactions of aryloxyacetaldehydes: a domino elimination/conjugate addition/acylation process for the synthesis of substituted coumarins.

Authors:  Eric M Phillips; Manabu Wadamoto; Howard S Roth; Andrew W Ott; Karl A Scheidt
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005

7.  Enantioselective thiourea-catalyzed additions to oxocarbenium ions.

Authors:  Sarah E Reisman; Abigail G Doyle; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2008-05-14       Impact factor: 15.419

8.  Catalytic enantioselective oxidative coupling of saturated ethers with carboxylic acid derivatives.

Authors:  Gang Wang; Xiaodong Xin; Zehua Wang; Gang Lu; Yudao Ma; Lei Liu
Journal:  Nat Commun       Date:  2019-02-04       Impact factor: 14.919

9.  Direct and Asymmetric Aldol Reactions of N-Azidoacetyl-1,3-thiazolidine-2-thione Catalyzed by Chiral Nickel(II) Complexes. A New Approach to the Synthesis of β-Hydroxy-α-Amino Acids.

Authors:  Saul F Teloxa; Miguel Mellado-Hidalgo; Stuart C D Kennington; Pedro Romea; Fèlix Urpí; Gabriel Aullón; Mercè Font-Bardia
Journal:  Chemistry       Date:  2022-05-26       Impact factor: 5.020

10.  3,3'-(1-Oxopropane-1,3-di-yl)bis-(1,3-thia-zolidine-2-thione) chloro-benzene hemisolvate.

Authors:  Christine Franzel; Andrew Purdy; Ray J Butcher
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-02-13
  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.