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

Helvetica chimica acta

Silicon??Directed Nazarov Reactions II. Preparation and Cyclization of β??Silyl??substituted Divinyl Ketones

TK Jones, SE Denmark

Index: Jones, Todd K.; Denmark, Scott E. Helvetica Chimica Acta, 1983 , vol. 66, # 8 p. 2377 - 2396

Full Text: HTML

Citation Number: 91

Abstract

Abstract Two general methods for the preparation of β-silyl-substituted divinyl ketones have been developed starting from either α, β-unsaturated aldehydes or simple ketones. Anhydrous FeCl 3 induces the cyclization to cyclopentenones under mild conditions and in good yields with predictable and complete control over the position of the double bond in the five-membered ring. The observed effects of substituents on rate can be explained by a ...

4-methyl-1-trimethylsilylpenta-1,4-dien-3-ol Structure

4-methyl-1-trim...

~75%

4-methyl-1-trimethylsilylpenta-1,4-dien-3-one Structure

4-methyl-1-trim...

2-(Bromovinyl)Trimethylsilane Structure

2-(Bromovinyl)T...

~%

4-methyl-1-trimethylsilylpenta-1,4-dien-3-one Structure

4-methyl-1-trim...

4-methyl-1-trimethylsilylhexa-1,4-dien-3-ol Structure

4-methyl-1-trim...

~92%

4-methyl-1-trimethylsilylhexa-1,4-dien-3-one Structure

4-methyl-1-trim...

2-(Bromovinyl)Trimethylsilane Structure

2-(Bromovinyl)T...

~%

4-methyl-1-trimethylsilylhexa-1,4-dien-3-one Structure

4-methyl-1-trim...

trans-3-(trimethylsilyl)acryl-aldehyde Structure

trans-3-(trimet...

~%

4-methyl-1-trimethylsilylhexa-1,4-dien-3-one Structure

4-methyl-1-trim...

1-phenyl-5-trimethylsilylpenta-1,4-dien-3-ol Structure

1-phenyl-5-trim...

~%

4-phenylcyclopent-2-en-1-one Structure

4-phenylcyclope...

2-(Bromovinyl)Trimethylsilane Structure

2-(Bromovinyl)T...

~%

1-(3-methylcyclohexen-1-yl)-3-trimethylsilylprop-2-en-1-one Structure

1-(3-methylcycl...

1-Cyclohexene-1-carboxaldehyde, 3-methyl- (9CI) Structure

1-Cyclohexene-1...

~%

1-(3-methylcyclohexen-1-yl)-3-trimethylsilylprop-2-en-1-one Structure

1-(3-methylcycl...

1-(cyclohexen-1-yl)prop-2-en-1-one Structure

1-(cyclohexen-1...

~%

2,3,3a,4,5,6-Hexahydro-(1H)-inden-1-one Structure

2,3,3a,4,5,6-He...

2,3,4,5,6,7-Hexahydro-1H-indene-1-one Structure

2,3,4,5,6,7-Hex...

1-(Cyclohex-1-enyl)prop-2-en-1-ol Structure

1-(Cyclohex-1-e...

~%

2,3,4,5,6,7-Hexahydro-1H-indene-1-one Structure

2,3,4,5,6,7-Hex...

cyclohexene carbaldehyde Structure

cyclohexene car...

~%

2,3,4,5,6,7-Hexahydro-1H-indene-1-one Structure

2,3,4,5,6,7-Hex...

Crotonaldehyde Structure

2-(Bromovinyl)Trimethylsilane Structure

2-(Bromovinyl)T...

~%

1-trimethylsilylhexa-1,4-dien-3-ol Structure

1-trimethylsily...

(E)-1-(3,4-dihydro-1-naphthyl)-3-trimethylsilyl-2-propen-1-ol Structure

(E)-1-(3,4-dihy...

~90%

1-naphthalen-1-yl-3-trimethylsilylprop-2-en-1-one Structure

1-naphthalen-1-...

trans-3-(trimethylsilyl)acryl-aldehyde Structure

trans-3-(trimet...

~%

1-naphthalen-1-yl-3-trimethylsilylprop-2-en-1-one Structure

1-naphthalen-1-...

1-tetralone (2,4,6-triisopropylbenzenesulfonyl)hydrazone Structure

1-tetralone (2,...

~%

1-naphthalen-1-yl-3-trimethylsilylprop-2-en-1-one Structure

1-naphthalen-1-...

3,4-Dihydronaphthalen-1(2H)-one Structure

3,4-Dihydronaph...

~%

1-naphthalen-1-yl-3-trimethylsilylprop-2-en-1-one Structure

1-naphthalen-1-...

trans-3-(trimethylsilyl)acryl-aldehyde Structure

trans-3-(trimet...

~%

1-(6-methylcyclohexen-1-yl)-3-trimethylsilylprop-2-en-1-one Structure

1-(6-methylcycl...

2-methylcyclohexanone (2,4,6-triisopropylphenyl)sulphonylhydrazone Structure

2-methylcyclohe...

~%

1-(6-methylcyclohexen-1-yl)-3-trimethylsilylprop-2-en-1-one Structure

1-(6-methylcycl...

2-Methylcyclohexanone Structure

2-Methylcyclohe...

~%

1-(6-methylcyclohexen-1-yl)-3-trimethylsilylprop-2-en-1-one Structure

1-(6-methylcycl...

1-(Cyclohex-1-enyl)prop-2-en-1-ol Structure

1-(Cyclohex-1-e...

~42%

1-(cyclohexen-1-yl)prop-2-en-1-one Structure

1-(cyclohexen-1...

cyclohexene carbaldehyde Structure

cyclohexene car...

~%

1-(cyclohexen-1-yl)prop-2-en-1-one Structure

1-(cyclohexen-1...

3-Pentanone Structure

~%

4-ethyl-1-trimethylsilylhexa-1,4-dien-3-ol Structure

4-ethyl-1-trime...

trans-3-(trimethylsilyl)acryl-aldehyde Structure

trans-3-(trimet...

3-pentanone (2,4,6-triisopropylbenzenesulfonyl)hydrazone Structure

3-pentanone (2,...

~%

4-ethyl-1-trimethylsilylhexa-1,4-dien-3-ol Structure

4-ethyl-1-trime...

Pinacolone Structure

~%

5,5-dimethyl-4-methylidene-1-trimethylsilylhex-1-en-3-ol Structure

5,5-dimethyl-4-...

4-methylidene-1-trimethylsilylhex-1-en-3-one Structure

4-methylidene-1...

~49%

5-ethylcyclopent-2-en-1-one Structure

5-ethylcyclopen...

4-methylidene-1-trimethylsilylhex-1-en-3-ol Structure

4-methylidene-1...

~%

5-ethylcyclopent-2-en-1-one Structure

5-ethylcyclopen...

Methylpropenal Structure

2-(Bromovinyl)Trimethylsilane Structure

2-(Bromovinyl)T...

~%

4-methyl-1-trimethylsilylpenta-1,4-dien-3-ol Structure

4-methyl-1-trim...

trans-2-Methyl-2-butenal Structure

trans-2-Methyl-...

2-(Bromovinyl)Trimethylsilane Structure

2-(Bromovinyl)T...

~%

4-methyl-1-trimethylsilylhexa-1,4-dien-3-ol Structure

4-methyl-1-trim...

Cinnamic aldehyde Structure

Cinnamic aldehyde

2-(Bromovinyl)Trimethylsilane Structure

2-(Bromovinyl)T...

~%

1-phenyl-5-trimethylsilylpenta-1,4-dien-3-ol Structure

1-phenyl-5-trim...

4-methylidene-1-trimethylsilylhex-1-en-3-ol Structure

4-methylidene-1...

~87%

4-methylidene-1-trimethylsilylhex-1-en-3-one Structure

4-methylidene-1...

trans-3-(trimethylsilyl)acryl-aldehyde Structure

trans-3-(trimet...

~%

4-methylidene-1-trimethylsilylhex-1-en-3-one Structure

4-methylidene-1...

1-trimethylsilylhexa-1,4-dien-3-ol Structure

1-trimethylsily...

~96%

1-trimethylsilylhexa-1,4-dien-3-one Structure

1-trimethylsily...

2-(Bromovinyl)Trimethylsilane Structure

2-(Bromovinyl)T...

~%

1-trimethylsilylhexa-1,4-dien-3-one Structure

1-trimethylsily...

1-naphthalen-1-yl-3-trimethylsilylprop-2-en-1-one Structure

1-naphthalen-1-...

~60%

2,3-DIHYDRO-1H-BENZ[E]INDEN-1-ONE Structure

2,3-DIHYDRO-1H-...

1-tetralone (2,4,6-triisopropylbenzenesulfonyl)hydrazone Structure

1-tetralone (2,...

~%

2,3-DIHYDRO-1H-BENZ[E]INDEN-1-ONE Structure

2,3-DIHYDRO-1H-...

3,4-Dihydronaphthalen-1(2H)-one Structure

3,4-Dihydronaph...

~%

2,3-DIHYDRO-1H-BENZ[E]INDEN-1-ONE Structure

2,3-DIHYDRO-1H-...

(E)-1-(3,4-dihydro-1-naphthyl)-3-trimethylsilyl-2-propen-1-ol Structure

(E)-1-(3,4-dihy...

~%

2,3-DIHYDRO-1H-BENZ[E]INDEN-1-ONE Structure

2,3-DIHYDRO-1H-...

(E)-1-(1-cyclopentenyl)-3-trimethylsilyl-2-propen-1-ol Structure

(E)-1-(1-cyclop...

~86%

1-(cyclopenten-1-yl)-3-trimethylsilylprop-2-en-1-one Structure

1-(cyclopenten-...

1-Cyclopentene-1-carbaldehyde Structure

1-Cyclopentene-...

~%

1-(cyclopenten-1-yl)-3-trimethylsilylprop-2-en-1-one Structure

1-(cyclopenten-...

2-(Bromovinyl)Trimethylsilane Structure

2-(Bromovinyl)T...

~%

1-(cyclopenten-1-yl)-3-trimethylsilylprop-2-en-1-one Structure

1-(cyclopenten-...

trans-3-(trimethylsilyl)acryl-aldehyde Structure

trans-3-(trimet...

~%

1-(cyclopenten-1-yl)-3-trimethylsilylprop-2-en-1-one Structure

1-(cyclopenten-...

Cyclopentanone Structure

~%

1-(cyclopenten-1-yl)-3-trimethylsilylprop-2-en-1-one Structure

1-(cyclopenten-...

4-ethyl-1-trimethylsilylhexa-1,4-dien-3-ol Structure

4-ethyl-1-trime...

~92%

4-ethyl-1-trimethylsilylhexa-1,4-dien-3-one Structure

4-ethyl-1-trime...

3-pentanone (2,4,6-triisopropylbenzenesulfonyl)hydrazone Structure

3-pentanone (2,...

~%

4-ethyl-1-trimethylsilylhexa-1,4-dien-3-one Structure

4-ethyl-1-trime...

3-Pentanone Structure

~%

4-ethyl-1-trimethylsilylhexa-1,4-dien-3-one Structure

4-ethyl-1-trime...

5,5-dimethyl-4-methylidene-1-trimethylsilylhex-1-en-3-ol Structure

5,5-dimethyl-4-...

~84%

5,5-dimethyl-4-methylidene-1-trimethylsilylhex-1-en-3-one Structure

5,5-dimethyl-4-...

Pinacolone Structure

~%

5,5-dimethyl-4-methylidene-1-trimethylsilylhex-1-en-3-one Structure

5,5-dimethyl-4-...

1-phenyl-5-trimethylsilylpenta-1,4-dien-3-ol Structure

1-phenyl-5-trim...

~90%

1-phenyl-5-trimethylsilylpenta-1,4-dien-3-one Structure

1-phenyl-5-trim...

2-(Bromovinyl)Trimethylsilane Structure

2-(Bromovinyl)T...

~%

1-phenyl-5-trimethylsilylpenta-1,4-dien-3-one Structure

1-phenyl-5-trim...

cyclopentanone (2,4,6-triisopropylbenzenesulfonyl)hydrazone Structure

cyclopentanone ...

~%

1-(cyclopenten-1-yl)-3-trimethylsilylprop-2-en-1-one Structure

1-(cyclopenten-...

(E)-1-(1-cyclohexenyl)-3-trimethylsilyl-2-propen-1-ol Structure

(E)-1-(1-cycloh...

~86%

1-(cyclohexen-1-yl)-3-trimethylsilylprop-2-en-1-one Structure

1-(cyclohexen-1...

cyclohexene carbaldehyde Structure

cyclohexene car...

~%

1-(cyclohexen-1-yl)-3-trimethylsilylprop-2-en-1-one Structure

1-(cyclohexen-1...

2-(Bromovinyl)Trimethylsilane Structure

2-(Bromovinyl)T...

~%

1-(cyclohexen-1-yl)-3-trimethylsilylprop-2-en-1-one Structure

1-(cyclohexen-1...

cyclohexanone 2,4,6-triisopropylbenzenesulfonyl hydrazone Structure

cyclohexanone 2...

~%

1-(cyclohexen-1-yl)-3-trimethylsilylprop-2-en-1-one Structure

1-(cyclohexen-1...

Cyclohexanone Structure

~%

1-(cyclohexen-1-yl)-3-trimethylsilylprop-2-en-1-one Structure

1-(cyclohexen-1...