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ON THE MECHANISM OF THE LEWIS ACID MEDIATED CLEAVAGE OF CHIRAL ACETALS
被引:51
作者
:
SAMMAKIA, T
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry and Biochemistry, University of Colorado, Colorado 80309-0215, Boulder
SAMMAKIA, T
SMITH, RS
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry and Biochemistry, University of Colorado, Colorado 80309-0215, Boulder
SMITH, RS
机构
:
[1]
Department of Chemistry and Biochemistry, University of Colorado, Colorado 80309-0215, Boulder
来源
:
JOURNAL OF ORGANIC CHEMISTRY
|
1992年
/ 57卷
/ 11期
关键词
:
D O I
:
10.1021/jo00037a010
中图分类号
:
O62 [有机化学];
学科分类号
:
070303 ;
081704 ;
摘要
:
The TiCl4-promoted cleavage of acetals has been shown to proceed by different mechanisms depending on the structure of the acetal, making it difficult to draw firm conclusions about the mechanism of related acetals based on model studies.
引用
收藏
页码:2997 / 3000
页数:4
相关论文
共 30 条
[1]
ALEXAKIS A, 1990, TETRAHEDRON-ASYMMETR, V1, P447
[2]
ASYMMETRIC-SYNTHESIS VIA ACETAL TEMPLATES .3. ON THE STEREOCHEMISTRY OBSERVED IN THE CYCLIZATION OF CHIRAL ACETALS OF POLYOLEFINIC ALDEHYDES - FORMATION OF OPTICALLY-ACTIVE HOMOALLYLIC ALCOHOLS
[J].
BARTLETT, PA
论文数:
0
引用数:
0
h-index:
0
机构:
STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
BARTLETT, PA
;
JOHNSON, WS
论文数:
0
引用数:
0
h-index:
0
机构:
STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
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;
ELLIOTT, JD
论文数:
0
引用数:
0
h-index:
0
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STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
ELLIOTT, JD
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1983,
105
(07)
:2088
-2089
[3]
STEREOMUTATION OF METHOXYCARBENIUM IONS .2. EXPERIMENTAL-EVIDENCE FOR AN INVERSION PROCESS
[J].
BLACKBURN, C
论文数:
0
引用数:
0
h-index:
0
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MCMASTER UNIV,DEPT CHEM,HAMILTON L8S 4M1,ONTARIO,CANADA
BLACKBURN, C
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CHILDS, RF
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0
引用数:
0
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MCMASTER UNIV,DEPT CHEM,HAMILTON L8S 4M1,ONTARIO,CANADA
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CREMER, D
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引用数:
0
h-index:
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MCMASTER UNIV,DEPT CHEM,HAMILTON L8S 4M1,ONTARIO,CANADA
CREMER, D
;
GAUSS, J
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0
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MCMASTER UNIV,DEPT CHEM,HAMILTON L8S 4M1,ONTARIO,CANADA
GAUSS, J
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1985,
107
(08)
:2442
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[4]
CONFORMATIONAL-ANALYSIS OF CHIRAL ALKENES AND OXONIUM IONS - ABINITIO MOLECULAR-ORBITAL CALCULATIONS AND AN IMPROVED MM2 FORCE-FIELD
[J].
BROEKER, JL
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CALIF LOS ANGELES, DEPT CHEM & BIOCHEM, LOS ANGELES, CA 90024 USA
BROEKER, JL
;
HOFFMANN, RW
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0
引用数:
0
h-index:
0
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UNIV CALIF LOS ANGELES, DEPT CHEM & BIOCHEM, LOS ANGELES, CA 90024 USA
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;
HOUK, KN
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UNIV CALIF LOS ANGELES, DEPT CHEM & BIOCHEM, LOS ANGELES, CA 90024 USA
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113
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ASYMMETRIC-SYNTHESIS OF GAMMA,GAMMA-DIALKYL-GAMMA-AMINOBUTYRIC ACID ANALOGS AND 2,2-DISUBSTITUTED PYRROLIDINES - CONTROL OF STEREOCHEMISTRY IN AMINAL RING-OPENING BY VARYING THE EXTENT OF ALLYLIC 1,3-STRAIN
[J].
BURGESS, LE
论文数:
0
引用数:
0
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0
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COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80523
COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80523
BURGESS, LE
;
MEYERS, AI
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h-index:
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COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80523
COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80523
MEYERS, AI
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113
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[6]
ASYMMETRIC-SYNTHESIS VIA CHIRAL ACETAL TEMPLATES .7. FURTHER-STUDIES ON THE CYANATION REACTION - THE USE OF ACETALS DERIVED FROM DIOLS WITH ONE CHIRAL CENTER
[J].
CHOI, VMF
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0
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0
机构:
STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
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;
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STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
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;
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STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
JOHNSON, WS
.
TETRAHEDRON LETTERS,
1984,
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(06)
:591
-594
[7]
STEREOMUTATION OF METHOXYCARBENIUM IONS .1. AN INVESTIGATION OF THE MECHANISM IN GASEOUS AND SOLUTION PHASES
[J].
CREMER, D
论文数:
0
引用数:
0
h-index:
0
机构:
MCMASTER UNIV, DEPT CHEM, HAMILTON L8S 4M1, ONTARIO, CANADA
MCMASTER UNIV, DEPT CHEM, HAMILTON L8S 4M1, ONTARIO, CANADA
CREMER, D
;
GAUSS, J
论文数:
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引用数:
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MCMASTER UNIV, DEPT CHEM, HAMILTON L8S 4M1, ONTARIO, CANADA
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;
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MCMASTER UNIV, DEPT CHEM, HAMILTON L8S 4M1, ONTARIO, CANADA
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MCMASTER UNIV, DEPT CHEM, HAMILTON L8S 4M1, ONTARIO, CANADA
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[J].
DENMARK, SE
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;
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.
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(26)
:9258
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[9]
MECHANISTIC AND STEREOCHEMICAL DIVERGENCE IN THE ALLYLSILANE-ACETAL ADDITION-REACTION
[J].
DENMARK, SE
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引用数:
0
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DENMARK, SE
;
WILLSON, TM
论文数:
0
引用数:
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WILLSON, TM
.
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1989,
111
(09)
:3475
-3476
[10]
ON THE STEREOSELECTIVE OPENING OF ACHIRAL DIOXANE ACETALS
[J].
DENMARK, SE
论文数:
0
引用数:
0
h-index:
0
机构:
Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana
DENMARK, SE
;
ALMSTEAD, NG
论文数:
0
引用数:
0
h-index:
0
机构:
Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana
ALMSTEAD, NG
.
JOURNAL OF ORGANIC CHEMISTRY,
1991,
56
(22)
:6458
-6467
←
1
2
3
→
共 30 条
[1]
ALEXAKIS A, 1990, TETRAHEDRON-ASYMMETR, V1, P447
[2]
ASYMMETRIC-SYNTHESIS VIA ACETAL TEMPLATES .3. ON THE STEREOCHEMISTRY OBSERVED IN THE CYCLIZATION OF CHIRAL ACETALS OF POLYOLEFINIC ALDEHYDES - FORMATION OF OPTICALLY-ACTIVE HOMOALLYLIC ALCOHOLS
[J].
BARTLETT, PA
论文数:
0
引用数:
0
h-index:
0
机构:
STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
BARTLETT, PA
;
JOHNSON, WS
论文数:
0
引用数:
0
h-index:
0
机构:
STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
JOHNSON, WS
;
ELLIOTT, JD
论文数:
0
引用数:
0
h-index:
0
机构:
STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
ELLIOTT, JD
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1983,
105
(07)
:2088
-2089
[3]
STEREOMUTATION OF METHOXYCARBENIUM IONS .2. EXPERIMENTAL-EVIDENCE FOR AN INVERSION PROCESS
[J].
BLACKBURN, C
论文数:
0
引用数:
0
h-index:
0
机构:
MCMASTER UNIV,DEPT CHEM,HAMILTON L8S 4M1,ONTARIO,CANADA
BLACKBURN, C
;
CHILDS, RF
论文数:
0
引用数:
0
h-index:
0
机构:
MCMASTER UNIV,DEPT CHEM,HAMILTON L8S 4M1,ONTARIO,CANADA
CHILDS, RF
;
CREMER, D
论文数:
0
引用数:
0
h-index:
0
机构:
MCMASTER UNIV,DEPT CHEM,HAMILTON L8S 4M1,ONTARIO,CANADA
CREMER, D
;
GAUSS, J
论文数:
0
引用数:
0
h-index:
0
机构:
MCMASTER UNIV,DEPT CHEM,HAMILTON L8S 4M1,ONTARIO,CANADA
GAUSS, J
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1985,
107
(08)
:2442
-2448
[4]
CONFORMATIONAL-ANALYSIS OF CHIRAL ALKENES AND OXONIUM IONS - ABINITIO MOLECULAR-ORBITAL CALCULATIONS AND AN IMPROVED MM2 FORCE-FIELD
[J].
BROEKER, JL
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CALIF LOS ANGELES, DEPT CHEM & BIOCHEM, LOS ANGELES, CA 90024 USA
BROEKER, JL
;
HOFFMANN, RW
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CALIF LOS ANGELES, DEPT CHEM & BIOCHEM, LOS ANGELES, CA 90024 USA
HOFFMANN, RW
;
HOUK, KN
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CALIF LOS ANGELES, DEPT CHEM & BIOCHEM, LOS ANGELES, CA 90024 USA
HOUK, KN
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1991,
113
(13)
:5006
-5017
[5]
ASYMMETRIC-SYNTHESIS OF GAMMA,GAMMA-DIALKYL-GAMMA-AMINOBUTYRIC ACID ANALOGS AND 2,2-DISUBSTITUTED PYRROLIDINES - CONTROL OF STEREOCHEMISTRY IN AMINAL RING-OPENING BY VARYING THE EXTENT OF ALLYLIC 1,3-STRAIN
[J].
BURGESS, LE
论文数:
0
引用数:
0
h-index:
0
机构:
COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80523
COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80523
BURGESS, LE
;
MEYERS, AI
论文数:
0
引用数:
0
h-index:
0
机构:
COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80523
COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80523
MEYERS, AI
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1991,
113
(26)
:9858
-9859
[6]
ASYMMETRIC-SYNTHESIS VIA CHIRAL ACETAL TEMPLATES .7. FURTHER-STUDIES ON THE CYANATION REACTION - THE USE OF ACETALS DERIVED FROM DIOLS WITH ONE CHIRAL CENTER
[J].
CHOI, VMF
论文数:
0
引用数:
0
h-index:
0
机构:
STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
CHOI, VMF
;
ELLIOTT, JD
论文数:
0
引用数:
0
h-index:
0
机构:
STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
ELLIOTT, JD
;
JOHNSON, WS
论文数:
0
引用数:
0
h-index:
0
机构:
STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305
JOHNSON, WS
.
TETRAHEDRON LETTERS,
1984,
25
(06)
:591
-594
[7]
STEREOMUTATION OF METHOXYCARBENIUM IONS .1. AN INVESTIGATION OF THE MECHANISM IN GASEOUS AND SOLUTION PHASES
[J].
CREMER, D
论文数:
0
引用数:
0
h-index:
0
机构:
MCMASTER UNIV, DEPT CHEM, HAMILTON L8S 4M1, ONTARIO, CANADA
MCMASTER UNIV, DEPT CHEM, HAMILTON L8S 4M1, ONTARIO, CANADA
CREMER, D
;
GAUSS, J
论文数:
0
引用数:
0
h-index:
0
机构:
MCMASTER UNIV, DEPT CHEM, HAMILTON L8S 4M1, ONTARIO, CANADA
MCMASTER UNIV, DEPT CHEM, HAMILTON L8S 4M1, ONTARIO, CANADA
GAUSS, J
;
CHILDS, RF
论文数:
0
引用数:
0
h-index:
0
机构:
MCMASTER UNIV, DEPT CHEM, HAMILTON L8S 4M1, ONTARIO, CANADA
MCMASTER UNIV, DEPT CHEM, HAMILTON L8S 4M1, ONTARIO, CANADA
CHILDS, RF
;
BLACKBURN, C
论文数:
0
引用数:
0
h-index:
0
机构:
MCMASTER UNIV, DEPT CHEM, HAMILTON L8S 4M1, ONTARIO, CANADA
MCMASTER UNIV, DEPT CHEM, HAMILTON L8S 4M1, ONTARIO, CANADA
BLACKBURN, C
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1985,
107
(08)
:2435
-2441
[8]
THE ORIGIN OF STEREOSELECTIVE OPENING OF CHIRAL DIOXANE AND DIOXOLANE ACETALS - SOLUTION STRUCTURE OF THEIR LEWIS ACID COMPLEXES
[J].
DENMARK, SE
论文数:
0
引用数:
0
h-index:
0
DENMARK, SE
;
WILLSON, TM
论文数:
0
引用数:
0
h-index:
0
WILLSON, TM
;
ALMSTEAD, NG
论文数:
0
引用数:
0
h-index:
0
ALMSTEAD, NG
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1989,
111
(26)
:9258
-9260
[9]
MECHANISTIC AND STEREOCHEMICAL DIVERGENCE IN THE ALLYLSILANE-ACETAL ADDITION-REACTION
[J].
DENMARK, SE
论文数:
0
引用数:
0
h-index:
0
DENMARK, SE
;
WILLSON, TM
论文数:
0
引用数:
0
h-index:
0
WILLSON, TM
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1989,
111
(09)
:3475
-3476
[10]
ON THE STEREOSELECTIVE OPENING OF ACHIRAL DIOXANE ACETALS
[J].
DENMARK, SE
论文数:
0
引用数:
0
h-index:
0
机构:
Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana
DENMARK, SE
;
ALMSTEAD, NG
论文数:
0
引用数:
0
h-index:
0
机构:
Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana
ALMSTEAD, NG
.
JOURNAL OF ORGANIC CHEMISTRY,
1991,
56
(22)
:6458
-6467
←
1
2
3
→