Literature DB >> 17760455

Asymmetric Eschenmoser-Claisen rearrangement for anti-beta-substituted gamma,delta-unsaturated amino acids.

Hongchang Qu1, Xuyuan Gu, Zhihua Liu, Byoung J Min, Victor J Hruby.   

Abstract

Optically active anti-beta-substituted gamma,delta-unsaturated amino acids are important synthetic building blocks in organic synthesis and for peptidomimetics. A novel asymmetric Eschenmoser-Claisen rearrangement with use of a C2-symmetric chiral auxiliary was developed to generate this type of amino acid. Excellent diastereoselectivities and high enantioselectivities (87-93% ee) were obtained after the chiral auxiliary was removed via iodolactonization/zinc reduction.

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Year:  2007        PMID： 17760455      PMCID： PMC2587277          DOI： 10.1021/ol701704h

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


  8 in total

1.  Application of the Ester Enolate Claisen Rearrangement in the Synthesis of Amino Acids Containing Quaternary Carbon Centers.

Authors:  Uli Kazmaier
Journal:  J Org Chem       Date:  1996-05-31       Impact factor: 4.354

2.  Chirality transferring [3,3] sigmatropic rearrangement of (1-Acyloxy-2-alkenyl)trianlkylsilane synthesis of optically active vinylsilane-containing alpha-amino acid.

Authors:  K Sakaguchi; H Suzuki; Y Ohfune
Journal:  Chirality       Date:  2001-07       Impact factor: 2.437

3.  A new antibiotic. Furanomycin, an isoleucine antagonist.

Authors:  K Katagiri; K Tori; Y Kimura; T Yoshida; T Nagasaki; H Minato
Journal:  J Med Chem       Date:  1967-11       Impact factor: 7.446

4.  Asymmetric chelated Claisen rearrangements in the presence of chiral ligands--scope and limitations.

Authors:  Uli Kazmaier; Heike Mues; Achim Krebs
Journal:  Chemistry       Date:  2002-04-15       Impact factor: 5.236

5.  Isolation and biosynthesis of cyclopentenylglycine, a novel nonproteinogenic amino acid in Flacourtiaceae.

Authors:  U Cramer; A G Rehfeldt; F Spener
Journal:  Biochemistry       Date:  1980-06-24       Impact factor: 3.162

6.  Parallel synthesis and biological evaluation of different sizes of bicyclo[2,3]-Leu-enkephalin analogues.

Authors:  Xuyuan Gu; Jinfa Ying; Byoung Min; James P Cain; Peg Davis; Patrick Willey; Edita Navratilova; Henry I Yamamura; Frank Porreca; Victor J Hruby
Journal:  Biopolymers       Date:  2005       Impact factor: 2.505

7.  Synthesis of Anti-beta-substituted gamma,delta-unsaturated amino acids via Eschenmoser-Claisen rearrangement.

Authors:  Hongchang Qu; Xuyuan Gu; Byoung J Min; Zhihua Liu; Victor J Hruby
Journal:  Org Lett       Date:  2006-09-14       Impact factor: 6.005

8.  Highly Enantioselective Claisen Rearrangement of Imidates Derived from Primary Allyl Alcohols.

Authors:  Peter Metz; Benno Hungerhoff
Journal:  J Org Chem       Date:  1997-06-27       Impact factor: 4.354
  8 in total
  5 in total

Review 1.  Peptidomimetics, a synthetic tool of drug discovery.

Authors:  Josef Vagner; Hongchang Qu; Victor J Hruby
Journal:  Curr Opin Chem Biol       Date:  2008-05-14       Impact factor: 8.822

Review 2.  Organic chemistry and biology: chemical biology through the eyes of collaboration.

Authors:  Victor J Hruby
Journal:  J Org Chem       Date:  2009-12-18       Impact factor: 4.354

3.  Enantioselective synthesis of anti-beta-substituted gamma,delta-unsaturated amino acids: a highly selective asymmetric thio-Claisen rearrangement.

Authors:  Zhihua Liu; Hongchang Qu; Xuyuan Gu; Byoung J Min; Gary S Nichol; Joel Nyberg; Victor J Hruby
Journal:  Org Lett       Date:  2008-08-15       Impact factor: 6.005

4.  Second-generation DBFOX ligands for the synthesis of beta-substituted alpha-amino acids via enantioselective radical conjugate additions.

Authors:  Biplab Banerjee; Steven G Capps; Junghoon Kang; Joshua W Robinson; Steven L Castle
Journal:  J Org Chem       Date:  2008-10-24       Impact factor: 4.354

5.  Enantioselective Allenoate-Claisen Rearrangement Using Chiral Phosphate Catalysts.

Authors:  Javier Miró; Tobias Gensch; Mario Ellwart; Seo-Jung Han; Hsin-Hui Lin; Matthew S Sigman; F Dean Toste
Journal:  J Am Chem Soc       Date:  2020-03-23       Impact factor: 15.419
  5 in total

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