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Literature DB >> 21476598

Catalytic asymmetric aza-Darzens reaction with a vaulted biphenanthrol magnesium phosphate salt.

Shawn E Larson¹, Guilong Li, Gerald B Rowland, Denise Junge, Rongcai Huang, H Lee Woodcock, Jon C Antilla.

Abstract

Conditions for a catalytic asymmetric aza-Darzens aziridine synthesis mediated by a vaulted biphenanthrol (VAPOL) magnesium phosphate salt is described. Using simple substrates, this methodology explores the scope and reactivity of a new magnesium catalyst for an aziridination reaction capable of building chirality and complexity simultaneously.

Entities: Chemical Gene

Mesh：

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Year: 2011 PMID： 21476598 PMCID： PMC3113529 DOI： 10.1021/ol200407r

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

34 in total

Review 1. Advances in methods and algorithms in a modern quantum chemistry program package.

Authors: Yihan Shao; Laszlo Fusti Molnar; Yousung Jung; Jörg Kussmann; Christian Ochsenfeld; Shawn T Brown; Andrew T B Gilbert; Lyudmila V Slipchenko; Sergey V Levchenko; Darragh P O'Neill; Robert A DiStasio; Rohini C Lochan; Tao Wang; Gregory J O Beran; Nicholas A Besley; John M Herbert; Ching Yeh Lin; Troy Van Voorhis; Siu Hung Chien; Alex Sodt; Ryan P Steele; Vitaly A Rassolov; Paul E Maslen; Prakashan P Korambath; Ross D Adamson; Brian Austin; Jon Baker; Edward F C Byrd; Holger Dachsel; Robert J Doerksen; Andreas Dreuw; Barry D Dunietz; Anthony D Dutoi; Thomas R Furlani; Steven R Gwaltney; Andreas Heyden; So Hirata; Chao-Ping Hsu; Gary Kedziora; Rustam Z Khalliulin; Phil Klunzinger; Aaron M Lee; Michael S Lee; Wanzhen Liang; Itay Lotan; Nikhil Nair; Baron Peters; Emil I Proynov; Piotr A Pieniazek; Young Min Rhee; Jim Ritchie; Edina Rosta; C David Sherrill; Andrew C Simmonett; Joseph E Subotnik; H Lee Woodcock; Weimin Zhang; Alexis T Bell; Arup K Chakraborty; Daniel M Chipman; Frerich J Keil; Arieh Warshel; Warren J Hehre; Henry F Schaefer; Jing Kong; Anna I Krylov; Peter M W Gill; Martin Head-Gordon
Journal: Phys Chem Chem Phys Date: 2006-06-12 Impact factor: 3.676

2. Chiral phosphoric acids: powerful organocatalysts for asymmetric addition reactions to imines.

Authors: Stephen J Connon
Journal: Angew Chem Int Ed Engl Date: 2006-06-12 Impact factor: 15.336

3. Asymmetric Mannich reaction of fluorinated ketoesters with a tryptophan-derived bifunctional thiourea catalyst.

Authors: Xiao Han; Jacek Kwiatkowski; Feng Xue; Kuo-Wei Huang; Yixin Lu
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

4. Catalytic Asymmetric Aziridination with Arylborate Catalysts Derived from VAPOL and VANOL Ligands This work was supported by the National Institutes of Health and was performed at the University of Chicago. VAPOL=2,2'-diphenyl-

Authors: Jon C. Antilla; William D. Wulff
Journal: Angew Chem Int Ed Engl Date: 2000-12-15 Impact factor: 15.336

Review 5. To protonate or alkylate? Stereoselective Brønsted acid catalysis of C-C bond formation using diazoalkanes.

Authors: Jeffrey N Johnston; Hubert Muchalski; Timothy L Troyer
Journal: Angew Chem Int Ed Engl Date: 2010-03-22 Impact factor: 15.336

6. Chiral lithium(I) binaphtholate salts for the enantioselective direct Mannich-type reaction with a change of syn/anti and absolute stereochemistry.

Authors: Manabu Hatano; Takahiro Horibe; Kazuaki Ishihara
Journal: J Am Chem Soc Date: 2010-01-13 Impact factor: 15.419

7. Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation.

Authors: Daisuke Uraguchi; Masahiro Terada
Journal: J Am Chem Soc Date: 2004-05-05 Impact factor: 15.419

8. Highly efficient asymmetric trans-selective aziridination of diazoacetamides and N-Boc-imines catalyzed by chiral Brønsted acids.

Authors: Xiaofei Zeng; Xin Zeng; Zhenjiang Xu; Min Lu; Guofu Zhong
Journal: Org Lett Date: 2009-07-16 Impact factor: 6.005

9. Trans-selective asymmetric aziridination of diazoacetamides and N-Boc imines catalyzed by axially chiral dicarboxylic acid.

Authors: Takuya Hashimoto; Nanase Uchiyama; Keiji Maruoka
Journal: J Am Chem Soc Date: 2008-10-11 Impact factor: 15.419

10. Mechanism of BINOL--phosphoric acid-catalyzed strecker reaction of benzyl imines.

Authors: Luis Simón; Jonathan M Goodman
Journal: J Am Chem Soc Date: 2009-03-25 Impact factor: 15.419

8 in total

1. Vaulted biaryls in catalysis: A structure-activity relationship guided tour of the immanent domain of the VANOL ligand.

Authors: Yong Guan; Zhensheng Ding; William D Wulff
Journal: Chemistry Date: 2013-10-02 Impact factor: 5.236

Catalytic asymmetric aza-Darzens reaction with a vaulted biphenanthrol magnesium phosphate salt.

Review 1. Advances in methods and algorithms in a modern quantum chemistry program package.

2. Chiral phosphoric acids: powerful organocatalysts for asymmetric addition reactions to imines.

3. Asymmetric Mannich reaction of fluorinated ketoesters with a tryptophan-derived bifunctional thiourea catalyst.

4. Catalytic Asymmetric Aziridination with Arylborate Catalysts Derived from VAPOL and VANOL Ligands This work was supported by the National Institutes of Health and was performed at the University of Chicago. VAPOL=2,2'-diphenyl-

Review 5. To protonate or alkylate? Stereoselective Brønsted acid catalysis of C-C bond formation using diazoalkanes.

6. Chiral lithium(I) binaphtholate salts for the enantioselective direct Mannich-type reaction with a change of syn/anti and absolute stereochemistry.

7. Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation.

8. Highly efficient asymmetric trans-selective aziridination of diazoacetamides and N-Boc-imines catalyzed by chiral Brønsted acids.

9. Trans-selective asymmetric aziridination of diazoacetamides and N-Boc imines catalyzed by axially chiral dicarboxylic acid.

10. Mechanism of BINOL--phosphoric acid-catalyzed strecker reaction of benzyl imines.

1. Vaulted biaryls in catalysis: A structure-activity relationship guided tour of the immanent domain of the VANOL ligand.

2. Efficient Access to Chiral Trisubstituted Aziridines via Catalytic Enantioselective Aza-Darzens Reactions.

3. Lithium BINOL phosphate catalyzed desymmetrization of meso-epoxides with aromatic thiols.

4. Direct asymmetric N-propargylation of indoles and carbazoles catalyzed by lithium SPINOL phosphate.

5. The Effect of Nano-Particles and Water Glass on the Water Stability of Magnesium Phosphate Cement Based Mortar.

6. Highly Efficient Darzens Reactions Mediated by Phosphazene Bases under Mild Conditions.

7. Asymmetric one-pot synthesis of 1,3-oxazolidines and 1,3-oxazinanes via hemiaminal intermediates.

8. Catalytic asymmetric α-Iminol rearrangement: new chiral platforms.