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

Organic letters

The palladium (II)-catalyzed Nazarov reaction

C Bee, E Leclerc, MA Tius

Index: Bee, Cisco; Leclerc, Eric; Tius, Marcus A. Organic Letters, 2003 , vol. 5, # 26 p. 4927 - 4930

Full Text: HTML

Citation Number: 75

Abstract

The PdCl 2 -catalyzed cyclization of α-alkoxy dienones leads to 2-hydroxycyclopentenones, whereas the Pd(OAc) 2 -catalyzed reaction leads to cross-conjugated cyclopentenones through an oxidative process. ... During the course of a survey of Lewis acids for use in a catalytic asymmetric version 1 of the Nazarov reaction, 2 we examined the effect of PdCl 2 (MeCN) 2 on dienone 1a. Cyclization to 2-hydroxycyclopentenone 2a took place in 91% yield in the presence of ...

2-methyl-1-morpholin-4-ylbut-2-en-1-one Structure

2-methyl-1-morp...

~%

hydroxydimethyl cyclopentenone Structure

hydroxydimethyl...

Ethoxyethene Structure

N/A Structure

~%

2-ethoxy-4-methylhepta-1,4-dien-3-one Structure

2-ethoxy-4-meth...

3,4-Dihydro-2H-pyran Structure

3,4-Dihydro-2H-pyran

2-METHYL-1-MORPHOLINOPROP-2-EN-1-ONE Structure

2-METHYL-1-MORP...

~%

1-(3,4-dihydro-2H-pyran-6-yl)-2-methylprop-2-en-1-one Structure

1-(3,4-dihydro-...

1-bromocyclohexene Structure

1-bromocyclohexene

(E)-2-methoxy-3,5-dimethyl-1-morpholinohex-2-en-1-one Structure

(E)-2-methoxy-3...

~%

1-(cyclohexen-1-yl)-2-methoxy-3,5-dimethylhex-2-en-1-one Structure

1-(cyclohexen-1...

4-Methyl-2-pentanone Structure

4-Methyl-2-pentanone

~%

1-(cyclohexen-1-yl)-2-methoxy-3,5-dimethylhex-2-en-1-one Structure

1-(cyclohexen-1...

3-hydroxy-2-methoxy-3,5-dimethyl-1-morpholin-4-ylhexan-1-one Structure

3-hydroxy-2-met...

~%

1-(cyclohexen-1-yl)-2-methoxy-3,5-dimethylhex-2-en-1-one Structure

1-(cyclohexen-1...

4-Methyl-2-pentanone Structure

4-Methyl-2-pentanone

~%

5-methoxy-2,3,6,8-tetramethylnona-2,5-dien-4-one Structure

5-methoxy-2,3,6...

3-hydroxy-2-methoxy-3,5-dimethyl-1-morpholin-4-ylhexan-1-one Structure

3-hydroxy-2-met...

~%

5-methoxy-2,3,6,8-tetramethylnona-2,5-dien-4-one Structure

5-methoxy-2,3,6...

4-ethoxy-2-methyl-1-phenylpenta-1,4-dien-3-one Structure

4-ethoxy-2-meth...

~98%

4-methyl-5-phenylpent-4-ene-2,3-dione Structure

4-methyl-5-phen...

(E)-2-methyl-1-morpholin-4-yl-3-phenylprop-2-en-1-one Structure

(E)-2-methyl-1-...

~%

4-methyl-5-phenylpent-4-ene-2,3-dione Structure

4-methyl-5-phen...

3-hydroxy-2-methoxy-3,5-dimethyl-1-morpholin-4-ylhexan-1-one Structure

3-hydroxy-2-met...

~%

(E)-2-methoxy-3,5-dimethyl-1-morpholinohex-2-en-1-one Structure

(E)-2-methoxy-3...

2-methoxy-3,5-dimethyl-1-morpholin-4-ylhex-2-en-1-one Structure

2-methoxy-3,5-d...

4-Methyl-2-pentanone Structure

4-Methyl-2-pentanone

~%

2-methoxy-3,5-dimethyl-1-morpholin-4-ylhex-2-en-1-one Structure

2-methoxy-3,5-d...

2-ethoxy-4-methylhepta-1,4-dien-3-one Structure

2-ethoxy-4-meth...

~55%

4-ethyl-2-hydroxy-3-methylcyclopent-2-en-1-one Structure

4-ethyl-2-hydro...

N/A Structure

~%

4-ethyl-2-hydroxy-3-methylcyclopent-2-en-1-one Structure

4-ethyl-2-hydro...

Ethoxyethene Structure

(E)-2-methyl-1-morpholin-4-yl-3-phenylprop-2-en-1-one Structure

(E)-2-methyl-1-...

~%

4-ethoxy-2-methyl-1-phenylpenta-1,4-dien-3-one Structure

4-ethoxy-2-meth...