Literature DB >> 16756289

Organocatalytic enantioselective synthesis of alpha-hydroxy phosphonates.

Sampak Samanta1, Cong-Gui Zhao.   

Abstract

Tertiary alpha-hydroxy phosphonates have been synthesized in good yields and high enantiomeric purity (up to 99% ee) through a novel l-proline-catalyzed cross aldol reaction of alpha-keto phosphonates and ketones.

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Year:  2006        PMID： 16756289      PMCID： PMC2535926          DOI： 10.1021/ja062091r

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  13 in total

1.  Application of fungi as biocatalysts for the reduction of diethyl 1-oxoalkylphosphonates in anhydrous hexane.

Authors:  Małorzata Brzezińska-Rodak; Ewa Zymańczyk-Duda; Paweał Kafarski; Barbara Lejczak
Journal:  Biotechnol Prog       Date:  2002 Nov-Dec

2.  A practical synthesis of (S)-2-cyclohexyl-2-phenylglycolic acid via organocatalytic asymmetric construction of a tetrasubstituted carbon center.

Authors:  Osamu Tokuda; Taichi Kano; Wei-Guo Gao; Tetsuya Ikemoto; Keiji Maruoka
Journal:  Org Lett       Date:  2005-10-27       Impact factor: 6.005

3.  Catalytic Asymmetric Synthesis of alpha-Hydroxy Phosphonates Using the Al-Li-BINOL Complex.

Authors:  Takayoshi Arai; Masahiro Bougauchi; Hiroaki Sasai; Masakatsu Shibasaki
Journal:  J Org Chem       Date:  1996-05-03       Impact factor: 4.354

4.  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

5.  Design of highly enantioselective organocatalysts based on molecular recognition.

Authors:  Zhuo Tang; Lin-Feng Cun; Xin Cui; Ai-Qiao Mi; Yao-Zhong Jiang; Liu-Zhu Gong
Journal:  Org Lett       Date:  2006-03-30       Impact factor: 6.005

6.  Antivaccinia activities of acyclic nucleoside phosphonate derivatives in epithelial cells and organotypic cultures.

Authors:  R Snoeck; A Holý; C Dewolf-Peeters; J Van Den Oord; E De Clercq; G Andrei
Journal:  Antimicrob Agents Chemother       Date:  2002-11       Impact factor: 5.191

7.  Catalytic concepts for the enantioselective synthesis of alpha-amino and alpha-hydroxy phosphonates.

Authors:  H Gröger; B Hammer
Journal:  Chemistry       Date:  2000-03-17       Impact factor: 5.236

8.  Dipeptide-catalyzed asymmetric aldol condensation of acetone with (N-alkylated) isatins.

Authors:  Gianluigi Luppi; Pier Giorgio Cozzi; Magda Monari; Bernard Kaptein; Quirinus B Broxterman; Claudia Tomasini
Journal:  J Org Chem       Date:  2005-09-02       Impact factor: 4.354

9.  Preparation of asymmetric alpha-ketophosphonates by [3,3]-sigmatropic shift of enolphosphonates.

Authors:  Kamyar Afarinkia; Andrew J Twist; Hiu-wan Yu
Journal:  J Org Chem       Date:  2004-09-17       Impact factor: 4.354

10.  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
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  20 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

Review 2.  The direct catalytic asymmetric aldol reaction.

Authors:  Barry M Trost; Cheyenne S Brindle
Journal:  Chem Soc Rev       Date:  2010-02-17       Impact factor: 54.564

3.  Quinidine thiourea-catalyzed aldol reaction of unactivated ketones: highly enantioselective synthesis of 3-alkyl-3-hydroxyindolin-2-ones.

Authors:  Qunsheng Guo; Mayur Bhanushali; Cong-Gui Zhao
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-03       Impact factor: 15.336

4.  Silver(I) triflate-catalyzed direct synthesis of N-PMP protected alpha-aminopropargylphosphonates from terminal alkynes.

Authors:  Rajasekhar Dodda; Cong-Gui Zhao
Journal:  Org Lett       Date:  2007-01-04       Impact factor: 6.005

5.  Organocatalytic enantioselective tandem aldol-cyclization reaction of α-isothiocyanato imides and activated carbonyl compounds.

Authors:  Jie Guang; Cong-Gui Zhao
Journal:  Tetrahedron Asymmetry       Date:  2011-06-15

6.  Organocatalytic Highly Enantioselective Tandem Michael-Knoevenagel Reaction for the Synthesis of Substituted Thiochromanes.

Authors:  Rajasekhar Dodda; Tanmay Mandal; Cong-Gui Zhao
Journal:  Tetrahedron Lett       Date:  2008-03-17       Impact factor: 2.415

7.  Enantioselective synthesis of alpha-aminopropargylphosphonates.

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

8.  Organocatalytic enantioselective synthesis of both diastereomers of alpha-hydroxyphosphinates.

Authors:  Sampak Samanta; Sandun Perera; Cong-Gui Zhao
Journal:  J Org Chem       Date:  2010-02-19       Impact factor: 4.354

9.  Asymmetric homoenolate additions to acyl phosphonates through rational design of a tailored N-heterocyclic carbene catalyst.

Authors:  Ki Po Jang; Gerri E Hutson; Ryne C Johnston; Elizabeth O McCusker; Paul H-Y Cheong; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2013-12-17       Impact factor: 15.419

10.  Diastereoselective and enantioselective synthesis of tertiary alpha-hydroxy phosphonates through hydrogen-bond catalysis.

Authors:  Vijaya Bhasker Gondi; Koji Hagihara; Viresh H Rawal
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336
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