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

Tetrahedron

Pentamethylcyclopentadienide in organic synthesis: nucleophilic addition of lithium pentamethylcyclopentadienide to carbonyl compounds and carbon–carbon bond …

M Uemura, K Yagi, M Iwasaki, K Nomura, H Yorimitsu…

Index: Uemura, Minoru; Yagi, Kazunari; Iwasaki, Masayuki; Nomura, Kenichi; Yorimitsu, Hideki; Oshima, Koichiro Tetrahedron, 2006 , vol. 62, # 15 p. 3523 - 3535

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Citation Number: 8

Abstract

Lithium pentamethylcyclopentadienide (C5Me5Li, Cp* Li) reacted with aromatic aldehyde to provide the corresponding carbinol in excellent yield. The carbinol returns to the parent aldehyde and pentamethylcyclopentadiene upon exposure to acid or due to heating. Chlorodimethylaluminum is essential as an additive to attain the nucleophilic addition of Cp* Li to aliphatic aldehyde. The carbinol derived from aliphatic aldehyde returns to the parent ...

7-hydroxy-7-(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)heptanenitrile Structure

7-hydroxy-7-(1,...

~73%

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

HEPTANENITRILE, 7-OXO- Structure

HEPTANENITRILE,...

10-chloro-1-(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)-1-decanol Structure

10-chloro-1-(1,...

~96%

10-chlorodecanal Structure

10-chlorodecanal

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

7-(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)-7-tridecanol Structure

7-(1,2,3,4,5-pe...

~97%

7-tridecanone Structure

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

(2-naphthyl)(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)methanol Structure

(2-naphthyl)(1,...

~85%

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

2-Naphthaldehyde Structure

2-Naphthaldehyde

(4-bromophenyl)(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)methanol Structure

(4-bromophenyl)...

~0%

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

4-Bromobenzaldehyde Structure

4-Bromobenzaldehyde

methyl 4-[(hydroxy)(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)methyl]benzoate Structure

methyl 4-[(hydr...

~0%

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

Methyl 4-formylbenzoate Structure

Methyl 4-formyl...

(2-naphthyl)(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)methanol Structure

(2-naphthyl)(1,...

~0%

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

2-Naphthaldehyde Structure

2-Naphthaldehyde

{4-[(hydroxy)(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)methyl]phenyl}(phenyl)methanone Structure

{4-[(hydroxy)(1...

~0%

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

4-Benzoylbenzaldehyde Structure

4-Benzoylbenzal...

10-chloro-1-(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)-1-decanol Structure

10-chloro-1-(1,...

~0%

10-chlorodecanal Structure

10-chlorodecanal

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

1-(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)-3-phenyl-1-propanol Structure

1-(1,2,3,4,5-pe...

~0%

3-Phenylpropanal Structure

3-Phenylpropanal

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

1-cyclohexyl-1-(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)-methanol Structure

1-cyclohexyl-1-...

~0%

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

Cyclohexanecarboxaldehyde Structure

Cyclohexanecarb...

methyl 6-hydroxy-6-(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)hexanoate Structure

methyl 6-hydrox...

~0%

Methyl 6-oxohexanoate Structure

Methyl 6-oxohex...

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

7-hydroxy-7-(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)heptanenitrile Structure

7-hydroxy-7-(1,...

~0%

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

HEPTANENITRILE, 7-OXO- Structure

HEPTANENITRILE,...

(4-buthoxyphenyl)(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)methanol Structure

(4-buthoxypheny...

~0%

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

4-Butoxybenzaldehyde Structure

4-Butoxybenzaldehyde

7-(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)-7-tridecanol Structure

7-(1,2,3,4,5-pe...

~99%

7-tridecanone Structure

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

1-(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)-3-phenyl-1-propanol Structure

1-(1,2,3,4,5-pe...

~%

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

methyl 6-hydroxy-6-(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)hexanoate Structure

methyl 6-hydrox...

~%

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

10-chloro-1-(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)-1-decanol Structure

10-chloro-1-(1,...

~%

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

1-(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)-1-dodecanol Structure

1-(1,2,3,4,5-pe...

~%

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

7-hydroxy-7-(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)heptanenitrile Structure

7-hydroxy-7-(1,...

~%

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

1-cyclohexyl-1-(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)-methanol Structure

1-cyclohexyl-1-...

~%

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

1-cyclohexyl-1-(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)-methanol Structure

1-cyclohexyl-1-...

~80%

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

Cyclohexanecarboxaldehyde Structure

Cyclohexanecarb...

(4-bromophenyl)(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)methanol Structure

(4-bromophenyl)...

~91%

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

4-Bromobenzaldehyde Structure

4-Bromobenzaldehyde

(4-buthoxyphenyl)(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)methanol Structure

(4-buthoxypheny...

~99%

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

4-Butoxybenzaldehyde Structure

4-Butoxybenzaldehyde

1-(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)-1-dodecanol Structure

1-(1,2,3,4,5-pe...

~0%

Lauryl aldehyde Structure

Lauryl aldehyde

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

4-Bromobenzaldehyde Structure

4-Bromobenzaldehyde

~%

4-[hydroxy(phenyl)methyl]benzaldehyde Structure

4-[hydroxy(phen...

{4-[(hydroxy)(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)methyl]phenyl}(phenyl)methanone Structure

{4-[(hydroxy)(1...

~89%

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

4-Benzoylbenzaldehyde Structure

4-Benzoylbenzal...

methyl 4-[(hydroxy)(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)methyl]benzoate Structure

methyl 4-[(hydr...

~91%

Pentamethylcyclopentadiene Structure

Pentamethylcycl...

Methyl 4-formylbenzoate Structure

Methyl 4-formyl...

Practical, high-yield, regioselective, rhodium-catalyzed hyd...

[Cuny, Gregory D.; Buchwald, Stephen L. Journal of the American Chemical Society, 1993 , vol. 115, # 5 p. 2066 - 2068]

Direct and chemoselective conversion of carboxylic acids int...

[Fujisawa, Tamotsu; Mori, Toshiki; Tsuge, Shoichi; Sato, Toshio Tetrahedron Letters, 1983 , vol. 24, # 14 p. 1543 - 1546]

Cerium (III) chloride-mediated reactions of sulfonamide dian...

[Johnson II, David C.; Widlanski, Theodore S. Journal of Organic Chemistry, 2003 , vol. 68, # 13 p. 5300 - 5309]

Cerium (III) chloride-mediated reactions of sulfonamide dian...

[Johnson II, David C.; Widlanski, Theodore S. Journal of Organic Chemistry, 2003 , vol. 68, # 13 p. 5300 - 5309]