Literature DB >> 20945849

Intramolecular hydroamination of dithioketene acetals: an easy route to cyclic amino acid derivatives.

Hai-Chao Xu1, Kevin D Moeller.   

Abstract

Catalytic intramolecular hydroamination of dithioketene acetals was developed for the synthesis of cyclic amino acid derivatives. Triggered by the addition of a catalytical amount of n-BuLi, the reaction proceeds to give proline and pipecolic acid derivatives in excellent yields and diastereoselectivity.

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Year:  2010        PMID： 20945849      PMCID： PMC3943425          DOI： 10.1021/ol102193x

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


  21 in total

1.  Conformationally restricted TRH analogues: constraining the pyroglutamate region.

Authors:  Jill C Simpson; Chris Ho; E F Berkley Shands; Marvin C Gershengorn; Garland R Marshall; Kevin D Moeller
Journal:  Bioorg Med Chem       Date:  2002-02       Impact factor: 3.641

2.  Mimicry of peptide backbone geometry and heteroatomic side-chain functionality: synthesis of enantiopure indolizidin-2-one amino acids possessing alcohol, acid, and azide functional groups.

Authors:  F Polyak; W D Lubell
Journal:  J Org Chem       Date:  2001-02-23       Impact factor: 4.354

3.  Synthesis of enantiopure 7-[3-azidopyl]indolizidin-2-one amino acid. A constrained mimic of the peptide backbone geometry and heteroatomic side-chain functionality of the ala-lys dipeptide.

Authors:  Z Feng; W D Lubell
Journal:  J Org Chem       Date:  2001-02-23       Impact factor: 4.354

Review 4.  Design, synthesis, and application of azabicyclo[X.Y.0]alkanone amino acids as constrained dipeptide surrogates and peptide mimics.

Authors:  Jérôme Cluzeau; William D Lubell
Journal:  Biopolymers       Date:  2005       Impact factor: 2.505

5.  Intramolecular anodic olefin coupling reactions: use of the reaction rate to control substrate/product selectivity.

Authors:  Hai-Chao Xu; Kevin D Moeller
Journal:  Angew Chem Int Ed Engl       Date:  2010-10-18       Impact factor: 15.336

6.  Synthesis and dopamine receptor modulating activity of 3-substituted gamma-lactam peptidomimetics of L-prolyl-L-leucyl-glycinamide.

Authors:  Kristine Dolbeare; Giuseppe F Pontoriero; Suresh K Gupta; Ram K Mishra; Rodney L Johnson
Journal:  J Med Chem       Date:  2003-02-27       Impact factor: 7.446

7.  Intramolecular anodic olefin coupling reactions and the synthesis of cyclic amines.

Authors:  Hai-Chao Xu; Kevin D Moeller
Journal:  J Am Chem Soc       Date:  2010-03-03       Impact factor: 15.419

8.  Three component coupling of alpha-iminoesters via umpolung addition of organometals: synthesis of alpha,alpha-disubstituted alpha-amino acids.

Authors:  Joshua S Dickstein; Michael W Fennie; Amber L Norman; Betty J Paulose; Marisa C Kozlowski
Journal:  J Am Chem Soc       Date:  2008-11-26       Impact factor: 15.419

9.  Catalytic asymmetric synthesis of cyclic alpha-alkyl-amino acid derivatives having a tetrasubstituted alpha-carbon.

Authors:  Yong-Gang Wang; Haruka Mii; Taichi Kano; Keiji Maruoka
Journal:  Bioorg Med Chem Lett       Date:  2009-04-14       Impact factor: 2.823

10.  An alternative convenient synthesis of piperidazine-3-carboxylic acid derivatives.

Authors:  Mamoru Kaname; Masae Yamada; Shigeyuki Yoshifuji; Haruki Sashida
Journal:  Chem Pharm Bull (Tokyo)       Date:  2009-01       Impact factor: 1.645
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  1 in total

1.  Anti-Markovnikov hydroamination of alkenes catalyzed by an organic photoredox system.

Authors:  Tien M Nguyen; David A Nicewicz
Journal:  J Am Chem Soc       Date:  2013-06-19       Impact factor: 15.419
  1 in total

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