Tetrahedron

An umpolung sulfoxide reagent for use as a functionalized benzyl carbanion equivalent

G Pinna, MC Bellucci, L Malpezzi, L Pisani, S Superchi…

Index: Pinna, Giovanni; Bellucci, Maria Cristina; Malpezzi, Luciana; Pisani, Laura; Superchi, Stefano; Volonterio, Alessandro; Zanda, Matteo Tetrahedron, 2011 , vol. 67, # 29 p. 5268 - 5281

Full Text: HTML

Citation Number: 5

Abstract

Abstract N-Methyl ortho-carbamoylaryl benzyl sulfoxides can be used as synthetic equivalents for α-hydroxy, α-chloro, and α-acetammido benzyl carbanions by means of a two- step sequence involving highly diastereoselective α-C-alkylation with alkyl halides followed by displacement of the sulfinyl residue (which can be recovered and recycled) by a hydroxyl, a chlorine or an acetamido, respectively, under non-oxidative Pummerer conditions. The ...

 Related Synthetic Route
N-methyl-2-(4-methyl-1-phenylpentylsulfinyl)benzamide Structure

1315275-23-0

N-methyl-2-(4-m...

~0%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

N/A Structure

1315275-30-9

N/A

N-methyl-2-(4-methyl-1-phenylpentylsulfinyl)benzamide Structure

1315275-23-0

N-methyl-2-(4-m...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

(E)-4-methyl-1-phenyl-1-pentanol Structure

89537-70-2

(E)-4-methyl-1-...

S-(-)-1-Phenyl-4-methylpentan-1-ol Structure

89537-67-7

S-(-)-1-Phenyl-...

2-(benzylthio)-N-methylbenzamide Structure

54705-19-0

2-(benzylthio)-...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

4-methyl-1-phenyl-pentan-1-ol Structure

2884-02-8

4-methyl-1-phen...

2-Mercapto-N-methylbenzamide Structure

20054-45-9

2-Mercapto-N-me...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

4-methyl-1-phenyl-pentan-1-ol Structure

2884-02-8

4-methyl-1-phen...

ortho-[(N-methyl)carbamoyl]phenyl benzyl sulfoxide Structure

54705-26-9

ortho-[(N-methy...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

4-methyl-1-phenyl-pentan-1-ol Structure

2884-02-8

4-methyl-1-phen...

2-(4-methoxybenzylsulfinyl)-N-methylbenzamide Structure

872220-83-2

2-(4-methoxyben...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

N/A Structure

1315275-26-3

N/A

2-(4-methoxybenzylsulfinyl)-N-methylbenzamide Structure

872220-83-2

2-(4-methoxyben...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

N/A Structure

1315275-28-5

N/A

2-(4-methoxybenzylsulfinyl)-N-methylbenzamide Structure

872220-83-2

2-(4-methoxyben...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

N/A Structure

77334-52-2

N/A

N/A Structure

872220-84-3

N/A

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

N/A Structure

1315275-27-4

N/A

N/A Structure

872220-84-3

N/A

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

N/A Structure

1315275-29-6

N/A

N/A Structure

872220-84-3

N/A

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

4-phenyl-1-[4-(trifluoromethyl)phenyl]butan-1-ol Structure

132777-02-7

4-phenyl-1-[4-(...

(S)-2-(benzylsulfinyl)-N-methylbenzamide Structure

1315275-16-1

(S)-2-(benzylsu...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

N/A Structure

1315275-30-9

N/A

2-(benzylthio)-N-methylbenzamide Structure

54705-19-0

2-(benzylthio)-...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

N/A Structure

1315275-30-9

N/A

2-(benzylthio)-N-methylbenzamide Structure

54705-19-0

2-(benzylthio)-...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

1-Phenylhex-5-en-1-ol Structure

144121-60-8

1-Phenylhex-5-e...

2-(benzylthio)-N-methylbenzamide Structure

54705-19-0

2-(benzylthio)-...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

1-chlorohex-5-enylbenzene Structure

61608-88-6

1-chlorohex-5-e...

2-[(4-methoxyphenyl)methylsulfanyl]benzoic acid Structure

101093-83-8

2-[(4-methoxyph...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

N/A Structure

1315275-26-3

N/A

2-[(4-methoxyphenyl)methylsulfanyl]benzoic acid Structure

101093-83-8

2-[(4-methoxyph...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

N/A Structure

1315275-28-5

N/A

2-[(4-methoxyphenyl)methylsulfanyl]benzoic acid Structure

101093-83-8

2-[(4-methoxyph...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

N/A Structure

77334-52-2

N/A

2-Mercapto-N-methylbenzamide Structure

20054-45-9

2-Mercapto-N-me...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

1-Phenylhex-5-en-1-ol Structure

144121-60-8

1-Phenylhex-5-e...

2-(4-trifluoromethyl-benzylsulfanyl)-benzoic acid Structure

1050884-48-4

2-(4-trifluorom...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

N/A Structure

1315275-27-4

N/A

2-(4-trifluoromethyl-benzylsulfanyl)-benzoic acid Structure

1050884-48-4

2-(4-trifluorom...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

N/A Structure

1315275-29-6

N/A

2-(4-trifluoromethyl-benzylsulfanyl)-benzoic acid Structure

1050884-48-4

2-(4-trifluorom...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

4-phenyl-1-[4-(trifluoromethyl)phenyl]butan-1-ol Structure

132777-02-7

4-phenyl-1-[4-(...

ortho-[(N-methyl)carbamoyl]phenyl benzyl sulfoxide Structure

54705-26-9

ortho-[(N-methy...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

1-Phenylhex-5-en-1-ol Structure

144121-60-8

1-Phenylhex-5-e...

ortho-[(N-methyl)carbamoyl]phenyl benzyl sulfoxide Structure

54705-26-9

ortho-[(N-methy...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

1-chlorohex-5-enylbenzene Structure

61608-88-6

1-chlorohex-5-e...

(S)-2-(benzylsulfinyl)-N-methylbenzamide Structure

1315275-16-1

(S)-2-(benzylsu...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

(E)-4-methyl-1-phenyl-1-pentanol Structure

89537-70-2

(E)-4-methyl-1-...

S-(-)-1-Phenyl-4-methylpentan-1-ol Structure

89537-67-7

S-(-)-1-Phenyl-...

2-(benzylthio)-N-methylbenzamide Structure

54705-19-0

2-(benzylthio)-...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

(E)-4-methyl-1-phenyl-1-pentanol Structure

89537-70-2

(E)-4-methyl-1-...

S-(-)-1-Phenyl-4-methylpentan-1-ol Structure

89537-67-7

S-(-)-1-Phenyl-...

Benzoic acid,2-[(phenylmethyl)thio]- Structure

1531-80-2

Benzoic acid,2-...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

(E)-4-methyl-1-phenyl-1-pentanol Structure

89537-70-2

(E)-4-methyl-1-...

S-(-)-1-Phenyl-4-methylpentan-1-ol Structure

89537-67-7

S-(-)-1-Phenyl-...

2-Mercapto-N-methylbenzamide Structure

20054-45-9

2-Mercapto-N-me...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

(E)-4-methyl-1-phenyl-1-pentanol Structure

89537-70-2

(E)-4-methyl-1-...

S-(-)-1-Phenyl-4-methylpentan-1-ol Structure

89537-67-7

S-(-)-1-Phenyl-...

Thiosalicylic acid Structure

147-93-3

Thiosalicylic acid

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

(E)-4-methyl-1-phenyl-1-pentanol Structure

89537-70-2

(E)-4-methyl-1-...

S-(-)-1-Phenyl-4-methylpentan-1-ol Structure

89537-67-7

S-(-)-1-Phenyl-...

2-(benzylthio)-N-methylbenzamide Structure

54705-19-0

2-(benzylthio)-...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

1-chlorohex-5-enylbenzene Structure

61608-88-6

1-chlorohex-5-e...

ortho-[(N-methyl)carbamoyl]phenyl benzyl sulfoxide Structure

54705-26-9

ortho-[(N-methy...

~%

2-Methyl-1,2-benzothiazol-3(2H)-one Structure

2527-66-4

2-Methyl-1,2-be...

1-chlorohex-5-enylbenzene Structure

61608-88-6

1-chlorohex-5-e...


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