Literature DB >> 18613692

A highly stereoselective synthesis of chiral alpha-amino-beta-lactams via the Kinugasa reaction employing ynamides.

Xuejun Zhang1, Richard P Hsung, Hongyan Li, Yu Zhang, Whitney L Johnson, Ruth Figueroa.   

Abstract

A highly stereoselective synthesis of chiral alpha-amino-beta-lactam through an ynamide-Kinugasa reaction is described. In addition, a mechanistic model is illustrated here to rationalize the observed diastereoselectivity, which depends on both the initial [3 + 2] cycloaddition step and the subsequent protonation for which both are highly selective.

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Year:  2008        PMID： 18613692      PMCID： PMC2587087          DOI： 10.1021/ol801257j

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


  11 in total

1.  Cu(I)/bis(azaferrocene)-catalyzed enantioselective synthesis of beta-lactams via couplings of alkynes with nitrones.

Authors:  Michael M-C Lo; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2002-05-01       Impact factor: 15.419

2.  Advances in the catalytic, asymmetric synthesis of beta-lactams.

Authors:  Stefan France; Anthony Weatherwax; Andrew E Taggi; Thomas Lectka
Journal:  Acc Chem Res       Date:  2004-08       Impact factor: 22.384

3.  beta-Lactam synthesis by the Kinugasa reaction.

Authors:  José Marco-Contelles
Journal:  Angew Chem Int Ed Engl       Date:  2004-04-19       Impact factor: 15.336

4.  A novel synthesis of beta-lactam fused cyclic enediynes by intramolecular Kinugasa reaction.

Authors:  Runa Pal; Amit Basak
Journal:  Chem Commun (Camb)       Date:  2006-06-07       Impact factor: 6.222

5.  Trisoxazoline/Cu(II)-promoted Kinugasa reaction. Enantioselective synthesis of beta-lactams.

Authors:  Meng-Chun Ye; Jian Zhou; Yong Tang
Journal:  J Org Chem       Date:  2006-04-28       Impact factor: 4.354

6.  The development of the first catalyzed reaction of ketenes and imines: catalytic, asymmetric synthesis of beta-lactams.

Authors:  Andrew E Taggi; Ahmed M Hafez; Harald Wack; Brandon Young; Dana Ferraris; Thomas Lectka
Journal:  J Am Chem Soc       Date:  2002-06-12       Impact factor: 15.419

7.  Enantioselective Staudinger synthesis of beta-lactams catalyzed by a planar-chiral nucleophile.

Authors:  Brian L Hodous; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2002-02-27       Impact factor: 15.419

8.  Chiral tris(oxazoline)/Cu(II) catalyzed coupling of terminal alkynes and nitrones.

Authors:  Meng-Chun Ye; Jian Zhou; Zheng-Zheng Huang; Yong Tang
Journal:  Chem Commun (Camb)       Date:  2003-10-21       Impact factor: 6.222

Review 9.  Alpha-imino esters: versatile substrates for the catalytic, asymmetric synthesis of alpha- and beta-amino acids and beta-lactams.

Authors:  Andrew E Taggi; Ahmed M Hafez; Thomas Lectka
Journal:  Acc Chem Res       Date:  2003-01       Impact factor: 22.384

10.  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
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  10 in total

Review 1.  Ynamides: a modern functional group for the new millennium.

Authors:  Kyle A DeKorver; Hongyan Li; Andrew G Lohse; Ryuji Hayashi; Zhenjie Lu; Yu Zhang; Richard P Hsung
Journal:  Chem Rev       Date:  2010-09-08       Impact factor: 60.622

2.  S3S63 Terminal Ynamides: Synthesis, Coupling Reactions and Additions to Common Electrophiles.

Authors:  Andrea M Cook; Christian Wolf
Journal:  Tetrahedron Lett       Date:  2015-05-06       Impact factor: 2.415

3.  Catalytic enantioselective nucleophilic addition of ynamides to aldehydes.

Authors:  Andrea M Cook; Christian Wolf
Journal:  Chem Commun (Camb)       Date:  2014-02-12       Impact factor: 6.222

4.  Synthesis of alpha-keto-imides via oxidation of ynamides.

Authors:  Ziyad F Al-Rashid; Whitney L Johnson; Richard P Hsung; Yonggang Wei; Pei-Yuan Yao; Renhei Liu; Kang Zhao
Journal:  J Org Chem       Date:  2008-10-21       Impact factor: 4.354

5.  Efficient Access to Multifunctional Trifluoromethyl Alcohols through Base-Free Catalytic Asymmetric C-C Bond Formation with Terminal Ynamides.

Authors:  Andrea M Cook; Christian Wolf
Journal:  Angew Chem Int Ed Engl       Date:  2016-01-25       Impact factor: 15.336

6.  A sequential metal-catalyzed C-N bond formation in the synthesis of 2-amido-indoles.

Authors:  Pei-Yuan Yao; Yu Zhang; Richard P Hsung; Kang Zhao
Journal:  Org Lett       Date:  2008-08-28       Impact factor: 6.005

7.  Synthesis of amidines using N-allyl ynamides. A palladium-catalyzed allyl transfer through an ynamido-pi-allyl complex.

Authors:  Yu Zhang; Kyle A DeKorver; Andrew G Lohse; Yan-Shi Zhang; Jian Huang; Richard P Hsung
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005

8.  A Rhodium(I)-Xylyl-BINAP Catalyzed Asymmetric Ynamide-[2 + 2 + 2] Cycloaddition in the Synthesis of Optically Enriched N,O-Biaryls.

Authors:  Jossian Oppenheimer; Whitney L Johnson; Ruth Figueroa; Ryuji Hayashi; Richard P Hsung
Journal:  Tetrahedron       Date:  2009-06-27       Impact factor: 2.457

Review 9.  Synthetic Approaches toward Monocyclic 3-Amino-β-lactams.

Authors:  Sari Deketelaere; Tuyen Van Nguyen; Christian V Stevens; Matthias D'hooghe
Journal:  ChemistryOpen       Date:  2017-06-05       Impact factor: 2.911

10.  Copper(I)-catalyzed nucleophilic addition of ynamides to acyl chlorides and activated N-heterocycles.

Authors:  Peng Zhang; Andrea M Cook; Yang Liu; Christian Wolf
Journal:  J Org Chem       Date:  2014-04-18       Impact factor: 4.354
  10 in total

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