Enantioselective Addition of Azlactones to Ethylene Sulfonyl Fluoride via Dual Catalysis

A dual copper/enamine catalytic system is found to enable an intermolecular enantioselective α-addition of various carbonyl nucleophiles to allenamides. Secondary amine catalysts allowed the highly enantioselective addition of aldehydes, while using primary amine catalysts led to the enantioselective addition of ketoester nucleophiles. The process was found to be highly regio-, stereo- and enantio-selective and represented the first allene hydrofunctionalization using an synergistic catalysis involving copper

Download Full-text

Concise Synthesis of GB22 by Endo-Selective Siloxycyclopropane Arylation

10.26434/chemrxiv.8263415.v1 ◽

2019 ◽

Cited By ~ 3

Author(s):

Hannah E. Burdge ◽

Takuya Oguma ◽

Takahiro Kawajiri ◽

Ryan Shenvi

Keyword(s):

Intramolecular Cyclization ◽

Cross Coupling ◽

Building Blocks ◽

Ring Expansion ◽

Dual Catalysis ◽

Acid Labile

<div><div><div><p>The first synthesis of GB22 was accomplished by a con- cise, modular route. Two building blocks converged in a novel sp3-sp2 attached-ring coupling that used Ir/Ni dual-catalysis to reverse the regioselectivity of siloxycy- clopropane arylation. This cross-coupling proved general to access β-substituted tetralones via ring-expansion of indanone-derived siloxycyclopropanes. The congested, bridging rings of the GB alkaloids were completed using an aluminum-HFIP complex that effected intramolecular cyclization of an acid-labile substrate.</p></div></div></div>

Download Full-text

Concise Synthesis of GB22 by Endo-Selective Siloxycyclopropane Arylation

10.26434/chemrxiv.8263415 ◽

2019 ◽

Author(s):

Hannah E. Burdge ◽

Takuya Oguma ◽

Takahiro Kawajiri ◽

Ryan Shenvi

Keyword(s):

Intramolecular Cyclization ◽

Cross Coupling ◽

Building Blocks ◽

Ring Expansion ◽

Dual Catalysis ◽

Acid Labile

<div><div><div><p>The first synthesis of GB22 was accomplished by a con- cise, modular route. Two building blocks converged in a novel sp3-sp2 attached-ring coupling that used Ir/Ni dual-catalysis to reverse the regioselectivity of siloxycy- clopropane arylation. This cross-coupling proved general to access β-substituted tetralones via ring-expansion of indanone-derived siloxycyclopropanes. The congested, bridging rings of the GB alkaloids were completed using an aluminum-HFIP complex that effected intramolecular cyclization of an acid-labile substrate.</p></div></div></div>

Download Full-text

Faculty Opinions recommendation of Rational targeting of active-site tyrosine residues using sulfonyl fluoride probes.

Faculty Opinions – Post-Publication Peer Review of the Biomedical Literature ◽

10.3410/f.725308994.793503330 ◽

2015 ◽

Author(s):

Thomas Kodadek

Keyword(s):

Active Site ◽

Tyrosine Residues ◽

Active Site Tyrosine ◽

Sulfonyl Fluoride

Download Full-text

Chiral Oxazaborolidines as Catalysts for the Enantioselective Addition of Diethylzinc to Aldehydes

10.21236/ada210543 ◽

1989 ◽

Author(s):

N. N. Joshi ◽

M. Srebnik ◽

H. C. Brown

Keyword(s):

Enantioselective Addition

Download Full-text

Highly enantioselective addition of sulfur-containing heterocycles to isatin-derived ketimines

Organic & Biomolecular Chemistry ◽

10.1039/c9ob01338e ◽

2019 ◽

Vol 17 (31) ◽

pp. 7309-7314 ◽

Cited By ~ 2

Author(s):

Michael Franc ◽

Michal Urban ◽

Ivana Císařová ◽

Jan Veselý

Keyword(s):

Heterocyclic Compounds ◽

Stereoselective Addition ◽

Enantioselective Addition ◽

Sulfur Containing

In this study, we report a highly stereoselective addition of sulfur-containing heterocyclic compounds to isatin-derived ketimines efficiently catalyzed by cinchonidine-derived bifunctional tertiary aminothiourea (1 mol%).

Download Full-text

Dimethylzinc-mediated enantioselective addition of terminal alkynes to 1,2-diketones using perhydro-1,3-benzoxazines as ligands

Organic & Biomolecular Chemistry ◽

10.1039/d1ob00249j ◽

2021 ◽

Author(s):

Elena Prieto ◽

Rebeca Infante ◽

Javier Nieto ◽

Celia Andres

Keyword(s):

Chiral Ligand ◽

Terminal Alkynes ◽

Conformationally Restricted ◽

Enantioselective Addition

A conformationally restricted perhydro-1,3-benzoxazine derived from (-)-8-aminomenthol behaves as a good chiral ligand in the dimethylzinc-mediated enantioselective monoaddition of aromatic and aliphatic terminal alkynes to 1,2-diketones. The corresponding α-hydroxyketones were...

Download Full-text