Literature DB >> 19812681

The catalytic asymmetric addition of alkyl- and aryl-zinc reagents to an isoxazole aldehyde.

Jared K Nelson1, Brendan Twamley, Trinidad J Villalobos, Nicholas R Natale.   

Abstract

Nucleophilic addition of alkyl- and aryl zinc reagents to a C(4) functionalized isoxazolyl aldehyde proceeded effectively with high enantioselectivity (85-94% e.e.). The amino alcohol catalyst (S)-2-piperidinyl-1,1,2-triphenyl ethanol (10) afforded the (R)-product 2b, as established by x-ray crystallography.

Entities:  

Year:  2008        PMID： 19812681      PMCID： PMC2598407          DOI： 10.1016/j.tetlet.2008.07.169

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  15 in total

1.  Directional preferences of intermolecular contacts to hydrophobic groups.

Authors:  J C Cole; R Taylor; M L Verdonk
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  1998-11-01

2.  Dual enantioselective control in asymmetric synthesis.

Authors:  Y H Kim
Journal:  Acc Chem Res       Date:  2001-12       Impact factor: 22.384

3.  Catalyzed asymmetric aryl transfer reactions to aldehydes with boronic acids as aryl source.

Authors:  Carsten Bolm; Jens Rudolph
Journal:  J Am Chem Soc       Date:  2002-12-18       Impact factor: 15.419

4.  New class of glutamate agonist structurally related to ibotenic acid.

Authors:  P Krogsgaard-Larsen; T Honoré; J J Hansen; D R Curtis; D Lodge
Journal:  Nature       Date:  1980-03-06       Impact factor: 49.962

Review 5.  Isoxazole ionotropic glutamate neurotransmitters.

Authors:  David J Burkhart; N R Natale
Journal:  Curr Med Chem       Date:  2005       Impact factor: 4.530

6.  Synthetic Utility of Epoxides for Chiral Functionalization of Isoxazoles.

Authors:  Jared K Nelson; Christopher T Burns; Miles P Smith; Brendan Twamley; N R Natale
Journal:  Tetrahedron Lett       Date:  2008-05-05       Impact factor: 2.415

7.  Catalytic asymmetric synthesis of glutamate analogues.

Authors:  David J Burkhart; Andrew R McKenzie; Jared K Nelson; Katherine I Myers; Xue Zhao; Kathy R Magnusson; Nicholas R Natale
Journal:  Org Lett       Date:  2004-04-15       Impact factor: 6.005

8.  The MPEG effect: improving asymmetric processes by simple additives.

Authors:  Jens Rudolph; Nina Hermanns; Carsten Bolm
Journal:  J Org Chem       Date:  2004-05-28       Impact factor: 4.354

9.  A practical, enantioselective synthetic route to a key precursor to the tetracycline antibiotics.

Authors:  Jason D Brubaker; Andrew G Myers
Journal:  Org Lett       Date:  2007-08-11       Impact factor: 6.005

10.  Insight into the mechanism of the asymmetric addition of alkyl groups to aldehydes catalyzed by titanium-BINOLate species.

Authors:  Jaume Balsells; Timothy J Davis; Patrick Carroll; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2002-09-04       Impact factor: 15.419
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  1 in total

1.  Isoxazole analogues bind the system xc- transporter: structure-activity relationship and pharmacophore model.

Authors:  Sarjubhai A Patel; Trideep Rajale; Erin O'Brien; David J Burkhart; Jared K Nelson; Brendan Twamley; Alex Blumenfeld; Monika I Szabon-Watola; John M Gerdes; Richard J Bridges; Nicholas R Natale
Journal:  Bioorg Med Chem       Date:  2009-11-10       Impact factor: 3.641
  1 in total

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