Regional convergence in the reaction of heterosubstituted allylic carbanions via allylic aluminum and boron ate complexes

Y Yamamoto, H Yatagai, Y Saito

Index: Yamamoto, Yoshinori; Yatagai, Hidetaka; Saito, Yoshikazu; Maruyama, Kazuhiro Journal of Organic Chemistry, 1984 , vol. 49, # 6 p. 1096 - 1104

Full Text: HTML

Citation Number: 69

Abstract

The regiochemistry in reactions of heterosubstituted allylic carbanions (1) is highly controlled via allylic aluminum or boron “ate” complexes which direct both carbonyl compounds and reactive halides to the a-position with high regioselectivity. For example, carbonyl compounds react with the oxygen-(3), sulfur-(12), selenium-(20), and silicon-(25) substituted allylic carbanions at the a-position via the ate complexes. Although the ...

 Related Synthetic Route
2-prop-2-enylsulfanylpropane Structure

50996-72-0

2-prop-2-enylsu...

2-Octanone Structure

111-13-7

2-Octanone

~%

4-methyl-1-propan-2-ylsulfanyldec-1-en-4-ol Structure

70624-57-6

4-methyl-1-prop...

N/A Structure

88916-18-1

N/A

Detail
crotyl bromide Structure

4784-77-4

crotyl bromide

2-prop-2-enylsulfanylpropane Structure

50996-72-0

2-prop-2-enylsu...

~%

3-methyl-4-propan-2-ylsulfanylhexa-1,5-diene Structure

71535-38-1

3-methyl-4-prop...

1-propan-2-ylsulfanylhepta-1,5-diene Structure

72087-75-3

1-propan-2-ylsu...

Detail
2-prop-2-enylsulfanylpropane Structure

50996-72-0

2-prop-2-enylsu...

1-Chloro-2-butene Structure

591-97-9

1-Chloro-2-butene

~%

3-methyl-4-propan-2-ylsulfanylhexa-1,5-diene Structure

71535-38-1

3-methyl-4-prop...

1-propan-2-ylsulfanylhepta-1,5-diene Structure

72087-75-3

1-propan-2-ylsu...

Detail
crotyl bromide Structure

4784-77-4

crotyl bromide

2-prop-2-enylsulfanylpropane Structure

50996-72-0

2-prop-2-enylsu...

~%

3-methyl-4-propan-2-ylsulfanylhexa-1,5-diene Structure

71535-38-1

3-methyl-4-prop...

1-propan-2-ylsulfanylhepta-1,5-diene Structure

72087-75-3

1-propan-2-ylsu...

Detail
2-prop-2-enylsulfanylpropane Structure

50996-72-0

2-prop-2-enylsu...

1-Chloro-2-butene Structure

591-97-9

1-Chloro-2-butene

~%

3-methyl-4-propan-2-ylsulfanylhexa-1,5-diene Structure

71535-38-1

3-methyl-4-prop...

1-propan-2-ylsulfanylhepta-1,5-diene Structure

72087-75-3

1-propan-2-ylsu...

Detail
2-prop-2-enylsulfanylpropane Structure

50996-72-0

2-prop-2-enylsu...

1-Chloro-3-methyl-2-butene Structure

503-60-6

1-Chloro-3-meth...

~%

3,3-dimethyl-4-propan-2-ylsulfanylhexa-1,5-diene Structure

71535-36-9

3,3-dimethyl-4-...

6-methyl-3-propan-2-ylsulfanylhepta-1,5-diene Structure

88916-01-2

6-methyl-3-prop...

2-prop-2-enylsulfanylpropane Structure

50996-72-0

2-prop-2-enylsu...

3,3-Dimethylallyl bromide Structure

870-63-3

3,3-Dimethylall...

~%

6-methyl-3-propan-2-ylsulfanylhepta-1,5-diene Structure

88916-01-2

6-methyl-3-prop...

6-methyl-1-propan-2-ylsulfanylhepta-1,5-diene Structure

88916-05-6

6-methyl-1-prop...

Detail
2-prop-2-enylsulfanylpropane Structure

50996-72-0

2-prop-2-enylsu...

1-Chloro-3-methyl-2-butene Structure

503-60-6

1-Chloro-3-meth...

~%

3,3-dimethyl-4-propan-2-ylsulfanylhexa-1,5-diene Structure

71535-36-9

3,3-dimethyl-4-...

6-methyl-3-propan-2-ylsulfanylhepta-1,5-diene Structure

88916-01-2

6-methyl-3-prop...

1-prop-2-enylpyrrolidine Structure

24420-11-9

1-prop-2-enylpy...

Chlorotrimethylsilane Structure

75-77-4

Chlorotrimethyl...

~%

(3-(trimethylsilyl)-1-propen-1-yl)pyrrolidine Structure

88932-88-1

(3-(trimethylsi...

trimethyl(1-pyrrolidin-1-ylprop-2-enyl)silane Structure

88916-02-3

trimethyl(1-pyr...

2-prop-2-enylsulfanylpropane Structure

50996-72-0

2-prop-2-enylsu...

3,3-Dimethylallyl bromide Structure

870-63-3

3,3-Dimethylall...

~%

6-methyl-3-propan-2-ylsulfanylhepta-1,5-diene Structure

88916-01-2

6-methyl-3-prop...

6-methyl-1-propan-2-ylsulfanylhepta-1,5-diene Structure

88916-05-6

6-methyl-1-prop...

Detail
2-Propanethiol Structure

75-33-2

2-Propanethiol

ALLYL CHLORIDE Structure

107-05-1

ALLYL CHLORIDE

~91%

2-prop-2-enylsulfanylpropane Structure

50996-72-0

2-prop-2-enylsu...

2-prop-2-enylsulfanylpropane Structure

50996-72-0

2-prop-2-enylsu...

3,3-Dimethylallyl bromide Structure

870-63-3

3,3-Dimethylall...

~%

6-methyl-3-propan-2-ylsulfanylhepta-1,5-diene Structure

88916-01-2

6-methyl-3-prop...

6-methyl-1-propan-2-ylsulfanylhepta-1,5-diene Structure

88916-05-6

6-methyl-1-prop...

Detail
Chloromethyl methyl ether Structure

107-30-2

Chloromethyl me...

Allyl alcohol Structure

107-18-6

Allyl alcohol

~95%

3-(methoxymethoxy)prop-1-ene Structure

62322-45-6

3-(methoxymetho...

2-prop-2-enylsulfanylpropane Structure

50996-72-0

2-prop-2-enylsu...

allyl bromide Structure

106-95-6

allyl bromide

~%

1-propan-2-ylsulfanylhexa-1,5-diene Structure

50996-70-8

1-propan-2-ylsu...

3-propan-2-ylsulfanylhexa-1,5-diene Structure

71535-37-0

3-propan-2-ylsu...

2-prop-2-enylsulfanylpropane Structure

50996-72-0

2-prop-2-enylsu...

1-Chloro-2-butene Structure

591-97-9

1-Chloro-2-butene

~%

3-methyl-4-propan-2-ylsulfanylhexa-1,5-diene Structure

71535-38-1

3-methyl-4-prop...

3-propan-2-ylsulfanylhepta-1,5-diene Structure

72087-74-2

3-propan-2-ylsu...

crotyl bromide Structure

4784-77-4

crotyl bromide

2-prop-2-enylsulfanylpropane Structure

50996-72-0

2-prop-2-enylsu...

~%

3-methyl-4-propan-2-ylsulfanylhexa-1,5-diene Structure

71535-38-1

3-methyl-4-prop...

1-propan-2-ylsulfanylhepta-1,5-diene Structure

72087-75-3

1-propan-2-ylsu...

Detail
2-prop-2-enylsulfanylpropane Structure

50996-72-0

2-prop-2-enylsu...

1-Chloro-2-butene Structure

591-97-9

1-Chloro-2-butene

~%

3-methyl-4-propan-2-ylsulfanylhexa-1,5-diene Structure

71535-38-1

3-methyl-4-prop...

1-propan-2-ylsulfanylhepta-1,5-diene Structure

72087-75-3

1-propan-2-ylsu...

Detail
2-prop-2-enoxypropane Structure

6140-80-3

2-prop-2-enoxyp...

Cyclohexanone Structure

108-94-1

Cyclohexanone

~%

1-(1-propan-2-yloxyprop-2-enyl)cyclohexan-1-ol Structure

72087-65-1

1-(1-propan-2-y...

2-prop-2-enoxypropane Structure

6140-80-3

2-prop-2-enoxyp...

Cyclohexanone Structure

108-94-1

Cyclohexanone

~%

1-(3-propan-2-yloxyprop-2-enyl)cyclohexan-1-ol Structure

88915-88-2

1-(3-propan-2-y...

1-(1-propan-2-yloxyprop-2-enyl)cyclohexan-1-ol Structure

72087-65-1

1-(1-propan-2-y...

Crotonaldehyde Structure

123-73-9

Crotonaldehyde

2-prop-2-enoxypropane Structure

6140-80-3

2-prop-2-enoxyp...

~%

1-propan-2-yloxyhepta-1,5-dien-4-ol Structure

72087-67-3

1-propan-2-ylox...

N/A Structure

88915-89-3

N/A

Detail
2-prop-2-enylsulfanylpropane Structure

50996-72-0

2-prop-2-enylsu...

Cyclohexanone Structure

108-94-1

Cyclohexanone

~%

1-(3-propan-2-ylsulfanylprop-2-enyl)cyclohexan-1-ol Structure

70600-08-7

1-(3-propan-2-y...

1-(1-propan-2-ylsulfanylprop-2-enyl)cyclohexan-1-ol Structure

70600-06-5

1-(1-propan-2-y...

Isobutyraldehyde Structure

78-84-2

Isobutyraldehyde

Allyltrimethylsilane Structure

762-72-1

Allyltrimethylsilane

~%

2-methyl-6-trimethylsilylhex-5-en-3-ol Structure

85363-31-1

2-methyl-6-trim...

erythro-3-(trimethylsilyl)-4-hydroxy-5-methyl-1-hexene Structure

85125-25-3

erythro-3-(trim...

Detail
Diphenyldiselenide Structure

1666-13-3

Diphenyldiselenide

~%

6-phenylselanylhex-5-en-3-ol Structure

85363-35-5

6-phenylselanyl...

allyl phenyl selenide Structure

14370-82-2

allyl phenyl se...

Propionaldehyde Structure

123-38-6

Propionaldehyde

~%

6-phenylselanylhex-5-en-3-ol Structure

85363-35-5

6-phenylselanyl...

N/A Structure

88916-06-7

N/A

Detail
2-prop-2-enoxypropane Structure

6140-80-3

2-prop-2-enoxyp...

3,3-Dimethylallyl bromide Structure

870-63-3

3,3-Dimethylall...

~%

6-methyl-1-propan-2-yloxyhepta-1,5-diene Structure

68060-21-9

6-methyl-1-prop...

6-methyl-3-propan-2-yloxyhepta-1,5-diene Structure

68060-20-8

6-methyl-3-prop...

2-prop-2-enylsulfanylpropane Structure

50996-72-0

2-prop-2-enylsu...

Cyclohexanone Structure

108-94-1

Cyclohexanone

~%

1-(3-propan-2-ylsulfanylprop-2-enyl)cyclohexan-1-ol Structure

70600-08-7

1-(3-propan-2-y...

1-(1-propan-2-ylsulfanylprop-2-enyl)cyclohexan-1-ol Structure

70600-06-5

1-(1-propan-2-y...

2-prop-2-enylsulfanylpropane Structure

50996-72-0

2-prop-2-enylsu...

Butyraldehyde Structure

123-72-8

Butyraldehyde

~%

1-propan-2-ylsulfanylhept-1-en-4-ol Structure

72087-68-4

1-propan-2-ylsu...

N/A Structure

88916-16-9

N/A

Detail
Diphenyldiselenide Structure

1666-13-3

Diphenyldiselenide

~%

2-methyl-6-phenylselanylhex-5-en-3-ol Structure

85363-36-6

2-methyl-6-phen...

allyl phenyl selenide Structure

14370-82-2

allyl phenyl se...

Isobutyraldehyde Structure

78-84-2

Isobutyraldehyde

~%

2-methyl-6-phenylselanylhex-5-en-3-ol Structure

85363-36-6

2-methyl-6-phen...

2-Propanethiol Structure

75-33-2

2-Propanethiol

1-Chloro-2-butene Structure

591-97-9

1-Chloro-2-butene

~%

(E)-1-propan-2-ylsulfanylbut-2-ene Structure

88916-22-7

(E)-1-propan-2-...

1-propan-2-ylsulfanylbut-2-ene Structure

88915-94-0

1-propan-2-ylsu...

2-prop-2-enoxypropane Structure

6140-80-3

2-prop-2-enoxyp...

3,3-Dimethylallyl bromide Structure

870-63-3

3,3-Dimethylall...

~%

6-methyl-1-propan-2-yloxyhepta-1,5-diene Structure

68060-21-9

6-methyl-1-prop...

6-methyl-3-propan-2-yloxyhepta-1,5-diene Structure

68060-20-8

6-methyl-3-prop...

2-prop-2-enylsulfanylpropane Structure

50996-72-0

2-prop-2-enylsu...

1-Chloro-2-butene Structure

591-97-9

1-Chloro-2-butene

~%

3-methyl-4-propan-2-ylsulfanylhexa-1,5-diene Structure

71535-38-1

3-methyl-4-prop...

3-propan-2-ylsulfanylhepta-1,5-diene Structure

72087-74-2

3-propan-2-ylsu...

crotyl bromide Structure

4784-77-4

crotyl bromide

2-prop-2-enylsulfanylpropane Structure

50996-72-0

2-prop-2-enylsu...

~%

3-methyl-4-propan-2-ylsulfanylhexa-1,5-diene Structure

71535-38-1

3-methyl-4-prop...

1-propan-2-ylsulfanylhepta-1,5-diene Structure

72087-75-3

1-propan-2-ylsu...

Detail
2-prop-2-enylsulfanylpropane Structure

50996-72-0

2-prop-2-enylsu...

1-Chloro-2-butene Structure

591-97-9

1-Chloro-2-butene

~%

3-methyl-4-propan-2-ylsulfanylhexa-1,5-diene Structure

71535-38-1

3-methyl-4-prop...

1-propan-2-ylsulfanylhepta-1,5-diene Structure

72087-75-3

1-propan-2-ylsu...

Detail
2-prop-2-enoxypropane Structure

6140-80-3

2-prop-2-enoxyp...

Cyclohexanone Structure

108-94-1

Cyclohexanone

~%

1-(3-propan-2-yloxyprop-2-enyl)cyclohexan-1-ol Structure

88915-88-2

1-(3-propan-2-y...

1-(1-propan-2-yloxyprop-2-enyl)cyclohexan-1-ol Structure

72087-65-1

1-(1-propan-2-y...

2-Propanethiol Structure

75-33-2

2-Propanethiol

1-Chloro-2-butene Structure

591-97-9

1-Chloro-2-butene

~%

(E)-1-propan-2-ylsulfanylbut-2-ene Structure

88916-22-7

(E)-1-propan-2-...

1-propan-2-ylsulfanylbut-2-ene Structure

88915-94-0

1-propan-2-ylsu...

2-prop-2-enylsulfanylpropane Structure

50996-72-0

2-prop-2-enylsu...

allyl bromide Structure

106-95-6

allyl bromide

~%

1-propan-2-ylsulfanylhexa-1,5-diene Structure

50996-70-8

1-propan-2-ylsu...

3-propan-2-ylsulfanylhexa-1,5-diene Structure

71535-37-0

3-propan-2-ylsu...


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