Literature DB >> 20442797

Diastereoselective Synthesis of trans-beta-Lactams Using a Simple Multifunctional Catalyst.

Ciby J Abraham1, Daniel H Paull, Cajetan Dogo-Isonagie, Thomas Lectka.   

Abstract

A catalytic, highly diastereoselective process for the synthesis of trans-beta-lactams is reported. This system is based on a phosphonium fluoride precatalyst that both activates the nucleophile and directs the reaction process for high yield and diastereoselectivity.

Entities:  

Year:  2009        PMID： 20442797      PMCID： PMC2862499          DOI： 10.1055/s-0029-1217348

Source DB:  PubMed          Journal:  Synlett        ISSN： 0936-5214            Impact factor:   2.454


  12 in total

1.  Bifunctional asymmetric catalysis: a tandem nucleophile/Lewis acid promoted synthesis of beta-lactams.

Authors:  Stefan France; Harald Wack; Ahmed M Hafez; Andrew E Taggi; Daniel R Witsil; Thomas Lectka
Journal:  Org Lett       Date:  2002-05-02       Impact factor: 6.005

2.  An anionic nucleophilic catalyst system for the diastereoselective synthesis of trans-beta-lactams.

Authors:  Anthony Weatherwax; Ciby J Abraham; Thomas Lectka
Journal:  Org Lett       Date:  2005-08-04       Impact factor: 6.005

3.  Generation of ketenes from acid chlorides using NaH/crown ether shuttle-deprotonation for use in asymmetric catalysis.

Authors:  Andrew E Taggi; Harald Wack; Ahmed M Hafez; Stefan France; Thomas Lectka
Journal:  Org Lett       Date:  2002-02-21       Impact factor: 6.005

4.  Bifunctional Lewis acid-nucleophile-based asymmetric catalysis: mechanistic evidence for imine activation working in tandem with chiral enolate formation in the synthesis of beta-lactams.

Authors:  Stefan France; Meha H Shah; Anthony Weatherwax; Harald Wack; Justine P Roth; Thomas Lectka
Journal:  J Am Chem Soc       Date:  2005-02-02       Impact factor: 15.419

5.  Catalytic asymmetric Staudinger reactions to form beta-lactams: an unanticipated dependence of diastereoselectivity on the choice of the nitrogen substituent.

Authors:  Elaine C Lee; Brian L Hodous; Enda Bergin; Crystal Shih; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2005-08-24       Impact factor: 15.419

6.  Asymmetric cycloadditions of o-quinone methides employing chiral ammonium fluoride precatalysts.

Authors:  Ethan Alden-Danforth; Michael T Scerba; Thomas Lectka
Journal:  Org Lett       Date:  2008-10-14       Impact factor: 6.005

7.  A multistage, one-pot procedure mediated by a single catalyst: a new approach to the catalytic asymmetric synthesis of beta-amino acids.

Authors:  Ahmed M Hafez; Travis Dudding; Ty R Wagerle; Meha H Shah; Andrew E Taggi; Thomas Lectka
Journal:  J Org Chem       Date:  2003-07-25       Impact factor: 4.354

8.  Catalysis of 3-pyrrolidinecarboxylic acid and related pyrrolidine derivatives in enantioselective anti-Mannich-type reactions: importance of the 3-acid group on pyrrolidine for stereocontrol.

Authors:  Haile Zhang; Susumu Mitsumori; Naoto Utsumi; Masanori Imai; Noemi Garcia-Delgado; Maria Mifsud; Klaus Albertshofer; Paul Ha-Yeon Cheong; K N Houk; Fujie Tanaka; Carlos F Barbas
Journal:  J Am Chem Soc       Date:  2007-12-29       Impact factor: 15.419

Review 9.  Forty years of beta-lactam research.

Authors:  G N Rolinson
Journal:  J Antimicrob Chemother       Date:  1998-06       Impact factor: 5.790

10.  Design and synthesis of monocyclic beta-lactams as mechanism-based inhibitors of human cytomegalovirus protease.

Authors:  A D Borthwick; G Weingarten; T M Haley; M Tomaszewski; W Wang; Z Hu; J Bedard; H Jin; L Yuen; T S Mansour
Journal:  Bioorg Med Chem Lett       Date:  1998-02-17       Impact factor: 2.823
View more
  2 in total

1.  Catalytic, asymmetric reactions of ketenes and ketene enolates.

Authors:  Daniel H Paull; Anthony Weatherwax; Thomas Lectka
Journal:  Tetrahedron       Date:  2009-08-22       Impact factor: 2.457

2.  Direct functionalization of (un)protected tetrahydroisoquinoline and isochroman under iron and copper catalysis: two metals, two mechanisms.

Authors:  Michael Ghobrial; Michael Schnürch; Marko D Mihovilovic
Journal:  J Org Chem       Date:  2011-10-05       Impact factor: 4.354
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.