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

The Journal of Organic Chemistry

A stereospecific synthesis of hydroxyl-differentiated (E)-and (Z)-1, 4-enediols

RB Miller, MI Al-Hassan

Index: Miller, R. Bryan; Al-Hassan, Mohammed I. Journal of Organic Chemistry, 1983 , vol. 48, # 22 p. 4113 - 4116

Full Text: HTML

Citation Number: 18

Abstract

1 Et H 78 80 1 Me Me 77 54 1 Ph H 69 70 1(-CH2-) 5 80 51 2 Et H 75 81 2 Me Me 75 70 tetrahydrofuran to diisobutylaluminum hydride was employed in the hydroalumination step in order to preferentially coordinate the aluminum by the tetrahydrofuranyl oxygen in analogy to a recent observation by ZweifeL4 Under these conditions, no cleavage of the tetrahydropyranyl ether was observed, but unfortunately the yield of the desired product 1 ...

2-methyl-5-(oxan-2-yloxy)pent-3-en-2-ol Structure

2-methyl-5-(oxa...

~45%

4-methylpent-2-ene-1,4-diol Structure

4-methylpent-2-...

(E)-2-methyl-5-((tetrahydro-2H-pyran-2-yl)oxy)-3-(trimethylsilyl)pent-3-en-2-ol Structure

(E)-2-methyl-5-...

~%

4-methylpent-2-ene-1,4-diol Structure

4-methylpent-2-...

(Z)-6-((tetrahydro-2H-pyran-2-yl)oxy)hex-4-en-3-ol Structure

(Z)-6-((tetrahy...

~50%

hex-2-ene-1,4-diol Structure

hex-2-ene-1,4-diol

(E)-6-((tetrahydro-2H-pyran-2-yl)oxy)-4-(trimethylsilyl)hex-4-en-3-ol Structure

(E)-6-((tetrahy...

~%

hex-2-ene-1,4-diol Structure

hex-2-ene-1,4-diol

Tetrahydropyranyl Ether of (Z)-3-Bromo-3-(trimethylsilyl)-2-propen-1-ol Structure

Tetrahydropyran...

~85%

3-bromo-3-trimethylsilylprop-2-en-1-ol Structure

3-bromo-3-trime...

trimethyl-[3-(oxan-2-yloxy)prop-1-ynyl]silane Structure

trimethyl-[3-(o...

~%

3-bromo-3-trimethylsilylprop-2-en-1-ol Structure

3-bromo-3-trime...

Tetrahydropyranyl Ether of (E)-3-Bromo-3-(trimethylsilyl)-2-propen-1-ol Structure

Tetrahydropyran...

~%

3-bromo-3-trimethylsilylprop-2-en-1-ol Structure

3-bromo-3-trime...

Tetrahydropyranyl Ether of (E)-3-Bromo-3-(trimethylsilyl)-2-propen-1-ol Structure

Tetrahydropyran...

Propionaldehyde Structure

Propionaldehyde

~78%

6-(oxan-2-yloxy)-4-trimethylsilylhex-4-en-3-ol Structure

6-(oxan-2-yloxy...

trimethyl-[3-(oxan-2-yloxy)prop-1-ynyl]silane Structure

trimethyl-[3-(o...

~%

6-(oxan-2-yloxy)-4-trimethylsilylhex-4-en-3-ol Structure

6-(oxan-2-yloxy...

6-(oxan-2-yloxy)-4-trimethylsilylhex-4-en-3-ol Structure

6-(oxan-2-yloxy...

~79%

3-trimethylsilylhex-2-ene-1,4-diol Structure

3-trimethylsily...

trimethyl-[3-(oxan-2-yloxy)prop-1-ynyl]silane Structure

trimethyl-[3-(o...

~%

3-trimethylsilylhex-2-ene-1,4-diol Structure

3-trimethylsily...

Tetrahydropyranyl Ether of (E)-3-Bromo-3-(trimethylsilyl)-2-propen-1-ol Structure

Tetrahydropyran...

~%

3-trimethylsilylhex-2-ene-1,4-diol Structure

3-trimethylsily...

trimethyl-[3-(oxan-2-yloxy)prop-1-ynyl]silane Structure

trimethyl-[3-(o...

~%

4-methyl-3-trimethylsilylpent-2-ene-1,4-diol Structure

4-methyl-3-trim...

Tetrahydropyranyl Ether of (E)-3-Bromo-3-(trimethylsilyl)-2-propen-1-ol Structure

Tetrahydropyran...

~%

4-methyl-3-trimethylsilylpent-2-ene-1,4-diol Structure

4-methyl-3-trim...

(E)-2-methyl-5-((tetrahydro-2H-pyran-2-yl)oxy)-3-(trimethylsilyl)pent-3-en-2-ol Structure

(E)-2-methyl-5-...

~80%

2-methyl-5-(oxan-2-yloxy)pent-3-en-2-ol Structure

2-methyl-5-(oxa...

trimethyl-[3-(oxan-2-yloxy)prop-1-ynyl]silane Structure

trimethyl-[3-(o...

~%

2-methyl-5-(oxan-2-yloxy)pent-3-en-2-ol Structure

2-methyl-5-(oxa...

Tetrahydropyranyl Ether of (E)-3-Bromo-3-(trimethylsilyl)-2-propen-1-ol Structure

Tetrahydropyran...

~%

2-methyl-5-(oxan-2-yloxy)pent-3-en-2-ol Structure

2-methyl-5-(oxa...

Tetrahydropyranyl Ether of (Z)-3-Bromo-3-(trimethylsilyl)-2-propen-1-ol Structure

Tetrahydropyran...

~%

2-methyl-5-(oxan-2-yloxy)pent-3-en-2-ol Structure

2-methyl-5-(oxa...

(Z)-1-phenyl-4-((tetrahydro-2H-pyran-2-yl)oxy)-2-(trimethylsilyl)but-2-en-1-ol Structure

(Z)-1-phenyl-4-...

~67%

1-phenyl-2-trimethylsilylbut-2-ene-1,4-diol Structure

1-phenyl-2-trim...

trimethyl-[3-(oxan-2-yloxy)prop-1-ynyl]silane Structure

trimethyl-[3-(o...

~%

1-phenyl-2-trimethylsilylbut-2-ene-1,4-diol Structure

1-phenyl-2-trim...

Tetrahydropyranyl Ether of (E)-3-Bromo-3-(trimethylsilyl)-2-propen-1-ol Structure

Tetrahydropyran...

~%

1-phenyl-2-trimethylsilylbut-2-ene-1,4-diol Structure

1-phenyl-2-trim...

6-(oxan-2-yloxy)-4-trimethylsilylhex-4-en-3-ol Structure

6-(oxan-2-yloxy...

~60%

6-(oxan-2-yloxy)hex-4-en-3-ol Structure

6-(oxan-2-yloxy...

trimethyl-[3-(oxan-2-yloxy)prop-1-ynyl]silane Structure

trimethyl-[3-(o...

~%

6-(oxan-2-yloxy)hex-4-en-3-ol Structure

6-(oxan-2-yloxy...

Tetrahydropyranyl Ether of (E)-3-Bromo-3-(trimethylsilyl)-2-propen-1-ol Structure

Tetrahydropyran...

~%

6-(oxan-2-yloxy)hex-4-en-3-ol Structure

6-(oxan-2-yloxy...

Stereoselective synthesis of 2, 2, 6, 6-tetrasubstituted tet...

[Martin, David Diez; Marcos, Isidro S.; Basabe, Pilar; Romero, Ricardo E.; Moro, Rosalina F.; Lumeras, Wenceslao; Rodriguez, Lucena; Urones, Julio G. Synthesis, 2001 , # 7 p. 1013 - 1022]

Stereoselective synthesis of 2, 2, 6, 6-tetrasubstituted tet...

[Martin, David Diez; Marcos, Isidro S.; Basabe, Pilar; Romero, Ricardo E.; Moro, Rosalina F.; Lumeras, Wenceslao; Rodriguez, Lucena; Urones, Julio G. Synthesis, 2001 , # 7 p. 1013 - 1022]