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Literature DB >> 17020334

Organocatalytic highly enantioselective synthesis of secondary alpha-hydroxyphosphonates.

Abstract

[reaction: see text] The first organocatalytic cross aldol reaction of ketones and diethyl formylphosphonate hydrate has been realized by using readily available l-prolinamide as the catalyst. Secondary alpha-hydroxyphosphonates have been synthesized in high enantioselective (up to >99% ee) and good diastereoselectivity.

Entities: Chemical

Mesh：

Substances：

Year: 2006 PMID： 17020334 PMCID： PMC2525621 DOI： 10.1021/ol062005s

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

20 in total

1. Synthesis of an optically active C1-symmetric Al(salalen) complex and its application to the catalytic hydrophosphonylation of aldehydes.

Authors: Bunnai Saito; Tsutomu Katsuki
Journal: Angew Chem Int Ed Engl Date: 2005-07-18 Impact factor: 15.336

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. Highly enantioselective aerobic oxidation of alpha-hydroxyphosphonates catalyzed by chiral vanadyl(V) methoxides bearing N-salicylidene-alpha-aminocarboxylates.

Authors: Vijay D Pawar; Sampada Bettigeri; Shiue-Shien Weng; Jun-Qi Kao; Chien-Tien Chen
Journal: J Am Chem Soc Date: 2006-05-17 Impact factor: 15.419

6. 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

7. Enamine-based organocatalysis with proline and diamines: the development of direct catalytic asymmetric Aldol, Mannich, Michael, and Diels-alder reactions.

Authors: Wolfgang Notz; Fujie Tanaka; Carlos F Barbas
Journal: Acc Chem Res Date: 2004-08 Impact factor: 22.384

8. 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

9. Ozonolysis of vinyl compounds, CH2=CH-X, in aqueous solution--the chemistries of the ensuing formyl compounds and hydroperoxides.

Authors: Achim Leitzke; Roman Flyunt; Jacob A Theruvathu; Clemens von Sonntag
Journal: Org Biomol Chem Date: 2003-03-21 Impact factor: 3.876

10. An efficient route to chiral alpha- and beta-hydroxyalkanephosphonates.

Authors: Oscar Pàmies; Jan-E Bäckvall
Journal: J Org Chem Date: 2003-06-13 Impact factor: 4.354

16 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. 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

3. 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

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. 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

7. 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

8. 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

9. Enantioselective synthesis of alpha-aminopropargylphosphonates.

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

10. 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