Literature DB >> 21921970

Quinidine thiourea-catalyzed enantioselective synthesis of β-nitrophosphonates: Beneficial effects of molecular sieves.

Santhi Abbaraju1, Mayur Bhanushali, Cong-Gui Zhao.   

Abstract

An efficient method for enantioselective synthesis of β-nitrophosphonates via the Michael addition of diphenyl phosphite to nitroalkenes using the readily available quinidine thiourea organocatalyst has been developed. The desired β-nitrophosphonates were obtained in good ee values. Molecular sieves were found to be crucial for achieving high reproducible yields in this reaction.

Entities:  

Year:  2011        PMID： 21921970      PMCID： PMC3171176          DOI： 10.1016/j.tet.2011.07.059

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  20 in total

1.  Organocatalytic enantioselective synthesis of alpha-hydroxy phosphonates.

Authors:  Sampak Samanta; Cong-Gui Zhao
Journal:  J Am Chem Soc       Date:  2006-06-14       Impact factor: 15.419

2.  Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts.

Authors:  Benedek Vakulya; Szilárd Varga; Antal Csámpai; Tibor Soós
Journal:  Org Lett       Date:  2005-05-12       Impact factor: 6.005

3.  Enantioselective 1,4-addition reactions of diphenyl phosphite to nitroalkenes catalyzed by an axially chiral guanidine.

Authors:  Masahiro Terada; Takashi Ikehara; Hitoshi Ube
Journal:  J Am Chem Soc       Date:  2007-10-26       Impact factor: 15.419

4.  Lipophosphonoglycan of the plasma membrance of Acanthamoeba castellanii. Isolation from whole amoebae and identification of the water-soluble products of acid hydrolysis.

Authors:  E D Korn; D G Dearborn; P L Wright
Journal:  J Biol Chem       Date:  1974-06-10       Impact factor: 5.157

5.  Organocatalytic High Enantioselective Synthesis of β-Formyl-α-hydroxyphosphonates.

Authors:  Sandun Perera; Vijaya Kumar Naganaboina; Long Wang; Bin Zhang; Qunsheng Guo; Laxmidhar Rout; Cong-Gui Zhao
Journal:  Adv Synth Catal       Date:  2011-06-30       Impact factor: 5.837

6.  Thiourea catalyzed organocatalytic enantioselective Michael addition of diphenyl phosphite to nitroalkenes.

Authors:  Ana Alcaine; Eugenia Marqués-López; Pedro Merino; Tomás Tejero; Raquel P Herrera
Journal:  Org Biomol Chem       Date:  2011-02-25       Impact factor: 3.876

7.  Enantioselective synthesis of alpha-aminopropargylphosphonates.

Authors:  Rajasekhar Dodda; Cong-Gui Zhao
Journal:  Tetrahedron Lett       Date:  2007-06-18       Impact factor: 2.415

8.  Asymmetric Michael addition of alpha-hydroxyketones to nitroolefins catalyzed by chiral diamine.

Authors:  Olivier Andrey; Alexandre Alexakis; Gérald Bernardinelli
Journal:  Org Lett       Date:  2003-07-10       Impact factor: 6.005

9.  Aerobic photooxidation of phosphite esters using diorganotelluride catalysts.

Authors:  Makoto Oba; Yasunori Okada; Kozaburo Nishiyama; Wataru Ando
Journal:  Org Lett       Date:  2009-05-07       Impact factor: 6.005

10.  Inverse-electron-demand hetero-Diels-Alder reaction of beta,gamma-unsaturated alpha-ketophosphonates catalyzed by prolinal dithioacetals.

Authors:  Sampak Samanta; Jonathan Krause; Tanmay Mandal; Cong-Gui Zhao
Journal:  Org Lett       Date:  2007-06-09       Impact factor: 6.005
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  2 in total

1.  Synthesis of α-Arylphosphonates Using Copper-Catalyzed α-Arylation and Deacylative α-Arylation of β-Ketophosphonates.

Authors:  Laxmidhar Rout; Sridhar Regati; Cong-Gui Zhao
Journal:  Adv Synth Catal       Date:  2011-12-06       Impact factor: 5.837

2.  Organocatalyzed asymmetric Michael reaction of β-aryl-α-ketophosphonates and nitroalkenes.

Authors:  Jie Guang; John Cong-Gui Zhao
Journal:  Tetrahedron Lett       Date:  2013-10-16       Impact factor: 2.415
  2 in total

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