Literature DB >> 21918646

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

Sandun Perera1, Vijaya Kumar Naganaboina, Long Wang, Bin Zhang, Qunsheng Guo, Laxmidhar Rout, Cong-Gui Zhao.   

Abstract

The cross aldol reaction between enolizable aldehydes and α-ketophosphonates was achieved for the first time by using 9-amino-9-deoxy-epi-quinine as the catalyst. β-Formyl-α-hydroxyphosphonates were obtained in high to excellent enantioselectivities. The reaction works especially well with acetaldehyde, which is a tough substrate for organocatalyzed cross aldol reactions. The products were demonstrated to have anticancer activities.

Entities:  

Year:  2011        PMID： 21918646      PMCID： PMC3170695          DOI： 10.1002/adsc.201000835

Source DB:  PubMed          Journal:  Adv Synth Catal        ISSN： 1615-4150            Impact factor:   5.837


  43 in total

1.  New inhibitors of renin that contain novel phosphostatine Leu-Val replacements.

Authors:  J F Dellaria; R G Maki; H H Stein; J Cohen; D Whittern; K Marsh; D J Hoffman; J J Plattner; T J Perun
Journal:  J Med Chem       Date:  1990-02       Impact factor: 7.446

Review 2.  How to get the most out of two phosphorus chemistries. Studies on H-phosphonates.

Authors:  Jacek Stawinski; Adam Kraszewski
Journal:  Acc Chem Res       Date:  2002-11       Impact factor: 22.384

3.  CD73 on tumor cells impairs antitumor T-cell responses: a novel mechanism of tumor-induced immune suppression.

Authors:  Dachuan Jin; Jie Fan; Long Wang; Linda F Thompson; Aijie Liu; Benjamin J Daniel; Tahiro Shin; Tyler J Curiel; Bin Zhang
Journal:  Cancer Res       Date:  2010-02-23       Impact factor: 12.701

4.  Bisphosphonate treatment inhibits the growth of prostate cancer cells.

Authors:  M V Lee; E M Fong; F R Singer; R S Guenette
Journal:  Cancer Res       Date:  2001-03-15       Impact factor: 12.701

5.  Asymmetric aldol reaction of acetaldehyde and isatin derivatives for the total syntheses of ent-convolutamydine E and CPC-1 and a half fragment of madindoline A and B.

Authors:  Takahiko Itoh; Hayato Ishikawa; Yujiro Hayashi
Journal:  Org Lett       Date:  2009-09-03       Impact factor: 6.005

6.  Novel peptidyl phosphorus derivatives as inhibitors of human calpain I.

Authors:  M Tao; R Bihovsky; G J Wells; J P Mallamo
Journal:  J Med Chem       Date:  1998-09-24       Impact factor: 7.446

7.  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

8.  First enantioselective synthesis of (R)-convolutamydine B and E with N-(heteroarenesulfonyl)prolinamides.

Authors:  Noriyuki Hara; Shuichi Nakamura; Norio Shibata; Takeshi Toru
Journal:  Chemistry       Date:  2009-07-13       Impact factor: 5.236

9.  Enantioselective synthesis of beta-(3-hydroxypyrazol-1-yl) ketones using an organocatalyzed Michael addition reaction.

Authors:  Sanjib Gogoi; Cong-Gui Zhao; Derong Ding
Journal:  Org Lett       Date:  2009-06-04       Impact factor: 6.005

10.  Synthesis, in vitro antibacterial and antifungal evaluations of new alpha-hydroxyphosphonate and new alpha-acetoxyphosphonate derivatives of tetrazolo [1, 5-a] quinoline.

Authors:  Amol H Kategaonkar; Rajkumar U Pokalwar; Swapnil S Sonar; Vaibhav U Gawali; Bapurao B Shingate; Murlidhar S Shingare
Journal:  Eur J Med Chem       Date:  2009-12-24       Impact factor: 6.514
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  6 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.  Diametric stereocontrol in dynamic catalytic reduction of racemic acyl phosphonates: divergence from α-keto ester congeners.

Authors:  Michael T Corbett; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2013-01-08       Impact factor: 15.419

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

Authors:  Santhi Abbaraju; Mayur Bhanushali; Cong-Gui Zhao
Journal:  Tetrahedron       Date:  2011-09-30       Impact factor: 2.457

4.  Organocatalyzed enantioselective aldol reaction of 1H-pyrrole-2,3-diones.

Authors:  Mayur Bhanushali; Cong-Gui Zhao
Journal:  Tetrahedron Lett       Date:  2011-11-19       Impact factor: 2.415

5.  Acetylphosphonate as a surrogate of acetate or acetamide in organocatalyzed enantioselective aldol reactions.

Authors:  Jie Guang; Qunsheng Guo; John Cong-Gui Zhao
Journal:  Org Lett       Date:  2012-05-31       Impact factor: 6.005

6.  Recyclable Cu/C3N4 composite catalyzed AHA/A3 coupling reactions for the synthesis of propargylamines.

Authors:  Hang Xu; Jun Wang; Peng Wang; Xiyu Niu; Yidan Luo; Li Zhu; Xiaoquan Yao
Journal:  RSC Adv       Date:  2018-09-24       Impact factor: 4.036
  6 in total

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