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Literature DB >> 24123264

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

Yong Guan¹, Zhensheng Ding, William D Wulff.

Abstract

The active site in the BOROX catalyst is a chiral polyborate anion (boroxinate) that is assembled in situ from three equivalents of B(OPh)3 and one of the VANOL ligand by a molecule of substrate. The substrates are bound to the boroxinate by H bonds to oxygen atoms O1-O3. The effects of introducing substituents at each position of the naphthalene core of the VANOL ligand are systematically investigated in an aziridination reaction. Substituents in the 4,4'- and 8,8'-positions have a negative effect on catalyst performance, whereas, substituents in the 7- and 7'-positions have the biggest impact in a positive direction.

Entities: CellLine Chemical Disease Species

Keywords: asymmetric catalysis; biaryls; catalysis; structure-activity relationships

Mesh：

Substances：

Year: 2013 PMID： 24123264 PMCID： PMC3947456 DOI： 10.1002/chem.201302451

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

43 in total

1. 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

2. Multicomponent catalytic asymmetric aziridination of aldehydes.

Authors: Anil K Gupta; Munmun Mukherjee; William D Wulff
Journal: Org Lett Date: 2011-10-11 Impact factor: 6.005

3. 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

4. Double stereodifferentiation in the catalytic asymmetric aziridination of imines prepared from α-chiral amines.

Authors: Li Huang; Yu Zhang; Richard J Staples; Rui H Huang; William D Wulff
Journal: Chemistry Date: 2012-03-20 Impact factor: 5.236

5. Enantioselective zinc-mediated conjugate addition of terminal alkynes to enones.

Authors: Gonzalo Blay; Luz Cardona; José R Pedro; Amparo Sanz-Marco
Journal: Chemistry Date: 2012-08-31 Impact factor: 5.236

6. 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

7. Total synthesis of sedum alkaloids via catalyst controlled aza-Cope rearrangement and hydroformylation with formaldehyde.

Authors: Hong Ren; William D Wulff
Journal: Org Lett Date: 2012-12-24 Impact factor: 6.005

8. Chiral phosphoric acid-catalyzed desymmetrization of meso-aziridines with functionalized mercaptans.

Authors: Shawn E Larson; Juan C Baso; Guilong Li; Jon C Antilla
Journal: Org Lett Date: 2009-11-19 Impact factor: 6.005

9. Mapping the active site in a chemzyme: diversity in the N-substituent in the catalytic asymmetric aziridination of imines.

Authors: Yu Zhang; Zhenjie Lu; Aman Desai; William D Wulff
Journal: Org Lett Date: 2008-12-04 Impact factor: 6.005

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

5 in total

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

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

2. Multicomponent catalytic asymmetric aziridination of aldehydes.

3. 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-

4. Double stereodifferentiation in the catalytic asymmetric aziridination of imines prepared from α-chiral amines.

5. Enantioselective zinc-mediated conjugate addition of terminal alkynes to enones.

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

7. Total synthesis of sedum alkaloids via catalyst controlled aza-Cope rearrangement and hydroformylation with formaldehyde.

8. Chiral phosphoric acid-catalyzed desymmetrization of meso-aziridines with functionalized mercaptans.

9. Mapping the active site in a chemzyme: diversity in the N-substituent in the catalytic asymmetric aziridination of imines.

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

1. Ring Expansion of 1-Indanones to 2-Halo-1-naphthols as an Entry Point to Gilvocarcin Natural Products.

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

3. β-amino esters from the reductive ring opening of aziridine-2-carboxylates.

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

Review 5. Chiral Diol-Based Organocatalysts in Enantioselective Reactions.