e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

The Palladium??Catalyzed Aerobic Kinetic Resolution of Secondary Alcohols: Reaction Development, Scope, and Applications

DC Ebner, JT Bagdanoff, EM Ferreira…

Index: Ebner, David C.; Bagdanoff, Jeffrey T.; Ferreira, Eric M.; McFadden, Ryan M.; Caspi, Daniel D.; Trend, Raissa M.; Stoltz, Brian M. Chemistry - A European Journal, 2009 , vol. 15, # 47 p. 12978 - 12992

Full Text: HTML

Citation Number: 52

Abstract

Abstract The first palladium-catalyzed enantioselective oxidation of secondary alcohols has been developed, utilizing the readily available diamine (−)-sparteine as a chiral ligand and molecular oxygen as the stoichiometric oxidant. Mechanistic insights regarding the role of the base and hydrogen-bond donors have resulted in several improvements to the original system. Namely, addition of cesium carbonate and tert-butyl alcohol greatly enhances ...

(+/-)-methyl 3-hydroxy-2-methylcyclopent-1-enecarboxylate Structure

(+/-)-methyl 3-...

~%

1-Cyclopentene-1-carboxylicacid, 2-methyl-3-oxo-, methyl ester Structure

1-Cyclopentene-...

1-Cyclopentene-1-carboxylicacid,3-hydroxy-2-methyl-,methylester,(3S) Structure

1-Cyclopentene-...

TERT-BUTYL (3-HYDROXY-3-PHENYLPROPYL)CARBAMATE Structure

TERT-BUTYL (3-H...

~%

tert-Butyl (3-Oxo-3-phenylpropyl)carbamate Structure

tert-Butyl (3-O...

(S)-tert-Butyl (3-hydroxy-3-phenylpropyl)carbamate Structure

(S)-tert-Butyl ...

TERT-BUTYL (3-HYDROXY-3-PHENYLPROPYL)CARBAMATE Structure

TERT-BUTYL (3-H...

~%

tert-Butyl (3-Oxo-3-phenylpropyl)carbamate Structure

tert-Butyl (3-O...

(S)-tert-Butyl (3-hydroxy-3-phenylpropyl)carbamate Structure

(S)-tert-Butyl ...

piperonal Structure

METHYLLITHIUM Structure

~%

1,3-Benzodioxole-5-methanol,a-methyl- Structure

1,3-Benzodioxol...

(+/-)-1-(3,5-di-tert-butylphenyl)ethanol Structure

(+/-)-1-(3,5-di...

~99%

1-(3,5-di-tert-butylphenyl)ethanone Structure

1-(3,5-di-tert-...

(+/-)-1-(3,5-di-tert-butylphenyl)ethanol Structure

(+/-)-1-(3,5-di...

~%

(S)-(-)-1-(3,5-di-tert-butylphenyl)ethanol Structure

(S)-(-)-1-(3,5-...

1-(3,5-di-tert-butylphenyl)ethanone Structure

1-(3,5-di-tert-...

2-phenylcyclopent-2-en-1-ol Structure

2-phenylcyclope...

~%

N/A Structure

2-Phenylcyclopentene-3-one Structure

2-Phenylcyclope...

(+/-)-methyl 3-hydroxy-2-methylcyclopent-1-enecarboxylate Structure

(+/-)-methyl 3-...

~%

1-Cyclopentene-1-carboxylicacid, 2-methyl-3-oxo-, methyl ester Structure

1-Cyclopentene-...

1-Cyclopentene-1-carboxylicacid,3-hydroxy-2-methyl-,methylester,(3S) Structure

1-Cyclopentene-...

1-Cyclopropylethanol Structure

1-Cyclopropylethanol

~%

1-Cyclopropylethanone Structure

1-Cyclopropylet...

(s)-1-cyclopropylethanol Structure

(s)-1-cycloprop...

2-bromocyclopent-2-en-1-ol Structure

2-bromocyclopen...

~%

2-CYCLOPENTEN-1-ONE, 2-BROMO- Structure

2-CYCLOPENTEN-1...

(1S)-2-bromocyclopent-2-en-1-ol Structure

(1S)-2-bromocyc...

Furan Structure

Isopropoxyboronic acid pinacol ester Structure

Isopropoxyboron...

~81%

2-Furanboronic acid pinacol ester Structure

2-Furanboronic ...

N/A Structure

~%

N/A Structure

3-methyl-2-phenylcyclopent-2-en-1-one Structure

3-methyl-2-phen...

4-Bromotoluene Structure

Isopropoxyboronic acid pinacol ester Structure

Isopropoxyboron...

~97%

4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane Structure

4,4,5,5-Tetrame...

5-Bromo-1,3-benzodioxole Structure

5-Bromo-1,3-ben...

Isopropoxyboronic acid pinacol ester Structure

Isopropoxyboron...

~99%

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzodioxole Structure

5-(4,4,5,5-tetr...

(+/-)-2-bromocyclohex-2-enol Structure

(+/-)-2-bromocy...

~%

2-BROMOCYCLOHEX-2-ENONE Structure

2-BROMOCYCLOHEX...

(+/-)-2-bromocyclohex-2-enol Structure

(+/-)-2-bromocy...

2-IODOCYCLOPENT-2-ENONE Structure

2-IODOCYCLOPENT...

4-Methoxyphenylboronic Acid Pinacol Ester Structure

4-Methoxyphenyl...

~91%

2-(4-methoxyphenyl)cyclopent-2-en-1-one Structure

2-(4-methoxyphe...

2-Phenylcyclopentene-3-one Structure

2-Phenylcyclope...

~89%

2-phenylcyclopent-2-en-1-ol Structure

2-phenylcyclope...

(+/-)-2-phenylcyclohex-2-enol Structure

(+/-)-2-phenylc...

~%

2-phenylcyclohex-2-en-1-one Structure

2-phenylcyclohe...

(1S)-2-phenylcyclohex-2-en-1-ol Structure

(1S)-2-phenylcy...