Literature DB >> 15727475

Functionalization of alpha,beta-unsaturated esters and ketones: a facile and highly stereoselective one-pot approach to N-protected alpha,beta-dehydroamino acid derivatives.

Dianjun Chen1, Li Guo, Junying Liu, Sameer Kirtane, John F Cannon, Guigen Li.   

Abstract

A new, facile, and highly stereoselective protocol toward alpha,beta-dehydroamino acid derivatives has been developed. The one-pot synthesis was very convenient to perform by using the aminohalogenation reaction of alpha,beta-unsaturated esters and ketones followed by treatment with specific bases. Only two [2.2.2] bicyclic organic bases were found to be effective for this transformation. Good yields (58-68%) and excellent Z-selectivity were obtained for 12 examples. [reaction: see text]

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Year:  2005        PMID： 15727475     DOI： 10.1021/ol050002u

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


  5 in total

1.  Four-component domino reaction providing an easy access to multifunctionalized tricyclo[6.2.2.0(1,6)]dodecane derivatives.

Authors:  Bo Jiang; Chao Li; Feng Shi; Shu-Jiang Tu; Parminder Kaur; Walter Wever; Guigen Li
Journal:  J Org Chem       Date:  2010-05-07       Impact factor: 4.354

2.  Copper(I)-catalysed site-selective C(sp3)-H bond chlorination of ketones, (E)-enones and alkylbenzenes by dichloramine-T.

Authors:  Jianwen Jin; Yichao Zhao; Sara Helen Kyne; Kaveh Farshadfar; Alireza Ariafard; Philip Wai Hong Chan
Journal:  Nat Commun       Date:  2021-07-01       Impact factor: 14.919

3.  One-pot stereoselective synthesis of α,β-differentiated diamino esters via the sequence of aminochlorination, aziridination and intermolecular SN2 reaction.

Authors:  Yiwen Xiong; Ping Qian; Chenhui Cao; Haibo Mei; Jianlin Han; Guigen Li; Yi Pan
Journal:  Beilstein J Org Chem       Date:  2014-08-07       Impact factor: 2.883

4.  Stereoselectively synthesis and structural confirmation of dehydrodipeptides with dehydrobutyrine.

Authors:  Xia Tian; Linna Li; Jianrong Han; Xiaoli Zhen; Shouxin Liu
Journal:  Springerplus       Date:  2016-04-01

5.  Hypervalent Iodine (III) Catalyzed Regio- and Diastereoselective Aminochlorination of Tailored Electron Deficient Olefins via GAP Chemistry.

Authors:  Anis Ur Rahman; Nighat Zarshad; Peng Zhou; Weitao Yang; Guigen Li; Asad Ali
Journal:  Front Chem       Date:  2020-07-07       Impact factor: 5.221
  5 in total

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