Literature DB >> 15281738

Following an ISES lead: the first examples of asymmetric Ni(0)-mediated allylic amination.

David B Berkowitz1, Gourhari Maiti.   

Abstract

An ISES (in situ enzymatic screening) lead pointed to conditions (PMP N-protecting group, Ni(cod)(2) catalyst precursor) under which chiral, bidentate phosphines could promote Ni(0)-mediated allylic amination. Therefore, bidentate phosphines bearing central, axial, and planar chirality were examined with two model substrates of interest for PLP-enzyme inhibitor synthesis. In the best case, with (R)-MeO-BIPHEP, vinylglycinol derivative 2 was obtained in 75% ee (97% ee, one recrystallization) from 1. Further manipulation provided a Ni(0)-mediated entry into l-vinylglycine. [reaction: see text]

Entities:  

Mesh：

Substances：

Year:  2004        PMID： 15281738      PMCID： PMC6080629          DOI： 10.1021/ol049159x

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  16 in total

1.  Synthesis of (S)-alpha-cyclopropyl-4-phosphonophenylglycine.

Authors:  D Ma; W Zhu
Journal:  J Org Chem       Date:  2001-01-12       Impact factor: 4.354

2.  Treating cocaine addiction: from preclinical to clinical trial experience with gamma-vinyl GABA.

Authors:  Jonathan D Brodie; Emilia Figueroa; Stephen L Dewey
Journal:  Synapse       Date:  2003-12-01       Impact factor: 2.562

3.  L-Vinylglycine is an alternative substrate as well as a mechanism-based inhibitor of 1-aminocyclopropane-1-carboxylate synthase.

Authors:  L Feng; J F Kirsch
Journal:  Biochemistry       Date:  2000-03-14       Impact factor: 3.162

4.  α-VINYLLYSINE AND α-VINYLARGININE ARE TIME-DEPENDENT INHIBITORS OF THEIR COGNATE DECARBOXYLASES.

Authors:  David B Berkowitz; Wan-Jin Jahng; Michelle L Pedersen
Journal:  Bioorg Med Chem Lett       Date:  1996-09-17       Impact factor: 2.823

5.  Preparation and Synthetic Applications of (S)- and (R)-N-Boc-N,O-isopropylidene-alpha-methylserinals: Asymmetric Synthesis of (S)- and (R)-2-Amino-2-methylbutanoic Acids (Iva).

Authors:  Alberto Avenoza; Carlos Cativiela; Francisco Corzana; Jesús M. Peregrina; María M. Zurbano
Journal:  J Org Chem       Date:  1999-10-29       Impact factor: 4.354

6.  Mechanism for the desulfurization of L-cysteine catalyzed by the nifS gene product.

Authors:  L Zheng; R H White; V L Cash; D R Dean
Journal:  Biochemistry       Date:  1994-04-19       Impact factor: 3.162

7.  Unusual effects in the pd-catalyzed asymmetric allylic alkylations: synthesis of chiral chromans.

Authors:  Barry M Trost; Hong C Shen; Li Dong; Jean-Philippe Surivet
Journal:  J Am Chem Soc       Date:  2003-08-06       Impact factor: 15.419

8.  Inactivation of bacterial D-amino acid transaminases by the olefinic amino acid D-vinylglycine.

Authors:  T S Soper; J M Manning; P A Marcotte; C T Walsh
Journal:  J Biol Chem       Date:  1977-03-10       Impact factor: 5.157

9.  Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity.

Authors:  Carolyn E Anderson; Larry E Overman
Journal:  J Am Chem Soc       Date:  2003-10-15       Impact factor: 15.419

10.  First intramolecular enantioselective iridium-catalysed allylic aminations.

Authors:  Carolin Welter; Oliver Koch; Gunter Lipowsky; Günter Helmchen
Journal:  Chem Commun (Camb)       Date:  2004-03-05       Impact factor: 6.222
View more
  19 in total

1.  Exploiting Enzymatic Dynamic Reductive Kinetic Resolution (DYRKR) in Stereocontrolled Synthesis.

Authors:  Gregory A Applegate; David B Berkowitz
Journal:  Adv Synth Catal       Date:  2015-05-12       Impact factor: 5.837

2.  Halocarbocyclization entry into the oxabicyclo[4.3.1]decyl exomethylene-δ-lactone cores of linearifolin and zaluzanin A: exploiting combinatorial catalysis.

Authors:  Sandeep K Ginotra; Jacob A Friest; David B Berkowitz
Journal:  Org Lett       Date:  2012-02-08       Impact factor: 6.005

3.  "Cassette" in situ enzymatic screening identifies complementary chiral scaffolds for hydrolytic kinetic resolution across a range of epoxides.

Authors:  Sangeeta Dey; Douglas R Powell; Chunhua Hu; David B Berkowitz
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  Mechanism-based inactivation by aromatization of the transaminase BioA involved in biotin biosynthesis in Mycobaterium tuberculosis.

Authors:  Ce Shi; Todd W Geders; Sae Woong Park; Daniel J Wilson; Helena I Boshoff; Orishadipe Abayomi; Clifton E Barry; Dirk Schnappinger; Barry C Finzel; Courtney C Aldrich
Journal:  J Am Chem Soc       Date:  2011-10-24       Impact factor: 15.419

Review 5.  Contemporary screening approaches to reaction discovery and development.

Authors:  Karl D Collins; Tobias Gensch; Frank Glorius
Journal:  Nat Chem       Date:  2014-10       Impact factor: 24.427

6.  A new dehydrogenase from Clostridium acetobutylicum for asymmetric synthesis: dynamic reductive kinetic resolution entry into the Taxotère side chain.

Authors:  Gregory A Applegate; Ross W Cheloha; David L Nelson; David B Berkowitz
Journal:  Chem Commun (Camb)       Date:  2010-12-20       Impact factor: 6.222

7.  Synthesis of (±)-tetrapetalone A-Me aglycon.

Authors:  Peter N Carlsen; Tyler J Mann; Amir H Hoveyda; Alison J Frontier
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-07       Impact factor: 15.336

8.  Large-scale asymmetric synthesis of the bioprotective agent JP4-039 and analogs.

Authors:  Marie-Céline Frantz; Joshua G Pierce; Joan M Pierce; Li Kangying; Wan Qingwei; Matthew Johnson; Peter Wipf
Journal:  Org Lett       Date:  2011-03-31       Impact factor: 6.005

9.  In situ enzymatic screening (ISES) of P,N-ligands for Ni(0)-mediated asymmetric intramolecular allylic amination.

Authors:  David B Berkowitz; Weijun Shen; Gourhari Maiti
Journal:  Tetrahedron Asymmetry       Date:  2004-09-13

10.  Synthesis and Deployment of an Elusive Fluorovinyl Cation Equivalent: Access to Quaternary α-(1'-Fluoro)vinyl Amino Acids as Potential PLP Enzyme Inactivators.

Authors:  Christopher D McCune; Matthew L Beio; Jill M Sturdivant; Roberto de la Salud-Bea; Brendan M Darnell; David B Berkowitz
Journal:  J Am Chem Soc       Date:  2017-09-28       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.