Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Self-Assembly of a Library of Polyborate Chiral Anions for Asymmetric Catalytic Quinoline Reduction.

Literature DB >> 26034335

Self-Assembly of a Library of Polyborate Chiral Anions for Asymmetric Catalytic Quinoline Reduction.

Aman A Desai¹, Yong Guan¹, Aaron L Odom¹, Supriyo Majumder¹, William D Wulff¹.

Abstract

The 'template' polyborate BOROX catalysts are shown to mediate the asymmetric transfer hydrogenation of 2-quinolines. The rapid and simple generation of a large family of BOROX catalysts with significantly altered asymmetric pockets is described. A transition state model that explains the enantioselectivity is proposed.

Entities: Chemical Species

Keywords: BOROX catalyst; Hantzsch ester; VANOL; asymmetric transfer hydrogenation; boroxinate anion; polyborate; quinoline

Year: 2015 PMID： 26034335 PMCID： PMC4448761 DOI： 10.1016/j.tetlet.2015.02.063

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

Keyword Cloud
References

34 in total

Review 1. Recent advances in cooperative ion pairing in asymmetric organocatalysis.

Authors: Jean-François Brière; Sylvain Oudeyer; Vincent Dalla; Vincent Levacher
Journal: Chem Soc Rev Date: 2011-11-01 Impact factor: 54.564

2. Supramolecular catalysis beyond enzyme mimics.

Authors: Jurjen Meeuwissen; Joost N H Reek
Journal: Nat Chem Date: 2010-07-23 Impact factor: 24.427

3. Regulation of orthogonal functions in a dual catalyst system. Subservient role of a nonchiral Lewis acid in an asymmetric catalytic heteroatom Diels-Alder reaction.

Authors: Cory A Newman; Jon C Antilla; Pei Chen; Alexander V Predeus; Lee Fielding; William D Wulff
Journal: J Am Chem Soc Date: 2007-05-16 Impact factor: 15.419

4. Chiral phosphoric acid-catalyzed asymmetric transfer hydrogenation of quinolin-3-amines.

Authors: Xian-Feng Cai; Ran-Ning Guo; Guang-Shou Feng; Bo Wu; Yong-Gui Zhou
Journal: Org Lett Date: 2014-04-25 Impact factor: 6.005

5. How the binding of substrates to a chiral polyborate counterion governs diastereoselection in an aziridination reaction: H-bonds in equipoise.

Authors: Mathew J Vetticatt; Aman A Desai; William D Wulff
Journal: J Am Chem Soc Date: 2010-09-29 Impact factor: 15.419

10. BOROX catalysis: self-assembled amino-BOROX and imino-BOROX chiral Brønsted acids in a five component catalyst assembly/catalytic asymmetric aziridination.

Authors: Anil K Gupta; Munmun Mukherjee; Gang Hu; William D Wulff
Journal: J Org Chem Date: 2012-09-04 Impact factor: 4.354

Self-Assembly of a Library of Polyborate Chiral Anions for Asymmetric Catalytic Quinoline Reduction.

Review 1. Recent advances in cooperative ion pairing in asymmetric organocatalysis.

2. Supramolecular catalysis beyond enzyme mimics.

3. Regulation of orthogonal functions in a dual catalyst system. Subservient role of a nonchiral Lewis acid in an asymmetric catalytic heteroatom Diels-Alder reaction.

4. Chiral phosphoric acid-catalyzed asymmetric transfer hydrogenation of quinolin-3-amines.

5. How the binding of substrates to a chiral polyborate counterion governs diastereoselection in an aziridination reaction: H-bonds in equipoise.

6. A titanium-catalyzed three-component coupling to generate alpha,beta-unsaturated beta-iminoamines.

7. Three-component asymmetric catalytic Ugi reaction--concinnity from diversity by substrate-mediated catalyst assembly.

8. Isotope effects and mechanism of the asymmetric BOROX Brønsted acid catalyzed aziridination reaction.

9. A multicomponent coupling sequence for direct access to substituted quinolines.

10. BOROX catalysis: self-assembled amino-BOROX and imino-BOROX chiral Brønsted acids in a five component catalyst assembly/catalytic asymmetric aziridination.