Literature DB >> 18631372

Chiral N-phosphonyl imine chemistry: asymmetric additions of ester enolates for the synthesis of beta-amino acids.

Jianlin Han1, Teng Ai, Thao Nguyen, Guigen Li.   

Abstract

Chiral phosphonyl imines attached by 1-naphthyl protection group were found to react with lithium ester enolates smoothly and give chiral beta-amino esters in good yields (70-88%) and up to excellent diastereoselectivity (>99:1 dr). Triisopropoxytitanium (IV) chloride was found to enhance diastereoseletivity when used as the Lewis acid promoter. The chiral auxiliary can be readily removed by treating with HBr to give free amino esters. The absolute structure has been unambiguously determined by converting one of the products into an authentic sample. This reaction provides an easy access to beta-amino acid derivatives.

Entities:  

Mesh：

Substances：

Year:  2008        PMID： 18631372      PMCID： PMC2575089          DOI： 10.1111/j.1747-0285.2008.00682.x

Source DB:  PubMed          Journal:  Chem Biol Drug Des        ISSN： 1747-0277            Impact factor:   2.817


  18 in total

1.  Organocatalysis in conjugate amine additions: synthesis of beta-amino acid derivatives.

Authors:  Mukund P Sibi; Kennosuke Itoh
Journal:  J Am Chem Soc       Date:  2007-06-07       Impact factor: 15.419

2.  Practical synthesis of enantiomerically pure beta2-amino acids via proline-catalyzed diastereoselective aminomethylation of aldehydes.

Authors:  Yonggui Chi; Emily P English; William C Pomerantz; W Seth Horne; Leo A Joyce; Lane R Alexander; William S Fleming; Elizabeth A Hopkins; Samuel H Gellman
Journal:  J Am Chem Soc       Date:  2007-04-17       Impact factor: 15.419

3.  Enantioselective organocatalytic aminomethylation of aldehydes: a role for ionic interactions and efficient access to beta2-amino acids.

Authors:  Yonggui Chi; Samuel H Gellman
Journal:  J Am Chem Soc       Date:  2006-05-31       Impact factor: 15.419

4.  The tert-Butanesulfinyl Group: An Ideal Chiral Directing Group and Boc-Surrogate for the Asymmetric Synthesis and Applications of beta-Amino Acids.

Authors:  Tony P. Tang; Jonathan A. Ellman
Journal:  J Org Chem       Date:  1999-01-08       Impact factor: 4.354

Review 5.  Beta2-amino acids-syntheses, occurrence in natural products, and components of beta-peptides1,2.

Authors:  Gérald Lelais; Dieter Seebach
Journal:  Biopolymers       Date:  2004       Impact factor: 2.505

6.  Enantioselective synthesis of alpha,beta-disubstituted-beta-amino acids.

Authors:  Mukund P Sibi; Narayanasamy Prabagaran; Sandeep G Ghorpade; Craig P Jasperse
Journal:  J Am Chem Soc       Date:  2003-10-01       Impact factor: 15.419

7.  Radical addition to oxime ethers for asymmetric synthesis of beta-amino acid derivatives.

Authors:  Hideto Miyabe; Kayoko Fujii; Takeaki Naito
Journal:  Org Biomol Chem       Date:  2003-01-21       Impact factor: 3.876

8.  Highly efficient synthesis of beta-amino acid derivatives via asymmetric hydrogenation of unprotected enamines.

Authors:  Yi Hsiao; Nelo R Rivera; Thorsten Rosner; Shane W Krska; Eugenia Njolito; Fang Wang; Yongkui Sun; Joseph D Armstrong; Edward J J Grabowski; Richard D Tillyer; Felix Spindler; Christophe Malan
Journal:  J Am Chem Soc       Date:  2004-08-18       Impact factor: 15.419

9.  GPIIb/IIIa integrin antagonists with the new conformational restriction unit, trisubstituted beta-amino acid derivatives, and a substituted benzamidine structure.

Authors:  Y Hayashi; J Katada; T Harada; A Tachiki; K Iijima; Y Takiguchi; M Muramatsu; H Miyazaki; T Asari; T Okazaki; Y Sato; E Yasuda; M Yano; I Uno; I Ojima
Journal:  J Med Chem       Date:  1998-06-18       Impact factor: 7.446

10.  Chiral N-phosphonyl imine chemistry: asymmetric aza-Henry reaction.

Authors:  Adiseshu Kattuboina; Parminder Kaur; Teng Ai; Guigen Li
Journal:  Chem Biol Drug Des       Date:  2008-03       Impact factor: 2.817
View more
  8 in total

1.  REGIOSELECTIVE MULTICOMPONENT DOMINO REACTIONS PROVIDING RAPID AND EFFICIENT ROUTES TO FUSED ACRIDINES.

Authors:  Jin-Peng Zhang; Wei Fan; Jie Ding; Bo Jiang; Shu-Jiang Tu; Guigen Li
Journal:  Heterocycles       Date:  2013-12-17       Impact factor: 0.831

2.  GAP Peptide Synthesis via Design of New GAP Protecting Group: An Fmoc/tBu Synthesis of Thymopentin Free from Polymers, Chromatography and Recrystallization.

Authors:  Cole W Seifert; Armando Paniagua; Gabrielle A White; Lucy Cai; Guigen Li
Journal:  European J Org Chem       Date:  2016-03-08

3.  Asymmetric hydrophosphylation of chiral N-phosphonyl imines provides an efficient approach to chiral α-amino phosphonates.

Authors:  Parminder Kaur; Walter Wever; Trideep Rajale; Guigen Li
Journal:  Chem Biol Drug Des       Date:  2010-10       Impact factor: 2.817

4.  Asymmetric synthesis of α-amino-1,3-dithianes via chiral N-phosphonyl imine-based Umpolung reaction without using chromatography and recrystallization.

Authors:  Padmanabha V Kattamuri; Teng Ai; Suresh Pindi; Yinwei Sun; Peng Gu; Min Shi; Guigen Li
Journal:  J Org Chem       Date:  2011-03-15       Impact factor: 4.354

5.  N,N-DIIsopropyl-N-phosphonyl imines lead to efficient asymmetric synthesis of aziridine-2-carboxylic esters.

Authors:  Padmanabha V Kattamuri; Yiwen Xiong; Yi Pan; Guigen Li
Journal:  Org Biomol Chem       Date:  2013-05-28       Impact factor: 3.876

6.  Asymmetric C-C Bond Formation between Chiral N-Phosphonyl Imines and Ni(II)-Complex of Glycine Schiff Base Provides a GAP Synthesis of α,β-syn-Diamino Acid Derivatives.

Authors:  Hao Sun; Haowei Zhang; Jianlin Han; Yi Pan; Guigen Li
Journal:  European J Org Chem       Date:  2013-08-01

7.  Asymmetric Carbamoyl Anion Additions to Chiral N-Phosphonyl Imines via the GAP Chemistry Process and Stereoselectivity Enrichments.

Authors:  Cole W Seifert; Suresh Pindi; Guigen Li
Journal:  J Org Chem       Date:  2014-12-09       Impact factor: 4.354

8.  Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction.

Authors:  Yiwen Xiong; Haibo Mei; Lingmin Wu; Jianlin Han; Yi Pan; Guigen Li
Journal:  Beilstein J Org Chem       Date:  2014-03-13       Impact factor: 2.883
  8 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.