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REACTION OF ALLYLSTANNANES WITH ALPHA,BETA-UNSATURATED ACYLIRON COMPLEXES - STEREOSELECTIVE SYNTHESIS OF CYCLOPENTANE DERIVATIVES
被引:19
作者
:
HERNDON, JW
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry and Biochemistry, University of Maryland, College Park
HERNDON, JW
WU, C
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry and Biochemistry, University of Maryland, College Park
WU, C
HARP, JJ
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry and Biochemistry, University of Maryland, College Park
HARP, JJ
机构
:
[1]
Department of Chemistry and Biochemistry, University of Maryland, College Park
来源
:
ORGANOMETALLICS
|
1990年
/ 9卷
/ 12期
关键词
:
D O I
:
10.1021/om00162a030
中图分类号
:
O61 [无机化学];
学科分类号
:
070301 ;
081704 ;
摘要
:
The reaction between allylstannanes and α,β-unsaturated acyliron complexes has been examined. When the reaction is conducted in the presence of Lewis acids, [3 + 2] cycloaddition products are obtained with extremely high degrees of stereoselectivity. If the iron complex is alkylated prior to addition of the allylstannane, products resulting from the Michael addition of allyl anion are obtained. The [3 + 2] cycloadducts contain acyliron and organotin functionalities. The acyliron group is easily converted to the corresponding ester by treatment with N-bromosuccinimide in the presence of alcohols. The tributyltin group can be converted to a hydroxy group by treatment with bromine followed by treatment with peracids and amine bases; this transformation occurs with complete retention of stereochemistry. The high stereoselectivity can be explained by reaction through a synclinal orientation of allylstannane and the acyliron complex. The question of allylation vs cycloaddition has been attributed to the relative reactivity of the intermediate enolate derivatives. © 1990, American Chemical Society. All rights reserved.
引用
收藏
页码:3157 / 3171
页数:15
相关论文
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CHEMISTRY OF DICARBONYL ETA-5-CYCLOPENTADIENYL-ETA-1-ALLYLIRON AND ETA-2-OLEFINIRON COMPLEXES - PREPARATION AND CYCLOADDITION REACTIONS
CUTLER, A
论文数:
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引用数:
0
h-index:
0
机构:
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
CUTLER, A
EHNTHOLT, D
论文数:
0
引用数:
0
h-index:
0
机构:
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
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GIERING, WP
论文数:
0
引用数:
0
h-index:
0
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BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
GIERING, WP
LENNON, P
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h-index:
0
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BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
LENNON, P
RAGHU, S
论文数:
0
引用数:
0
h-index:
0
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BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
RAGHU, S
ROSAN, A
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引用数:
0
h-index:
0
机构:
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
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ROSENBLUM, M
论文数:
0
引用数:
0
h-index:
0
机构:
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
ROSENBLUM, M
TANCREDE, J
论文数:
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引用数:
0
h-index:
0
机构:
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
TANCREDE, J
WELLS, D
论文数:
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引用数:
0
h-index:
0
机构:
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
WELLS, D
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1976,
98
(12)
: 3495
-
3507
[12]
SCOPE AND STEREOCHEMICAL COURSE OF THE (TRIMETHYLSILYL)CYCLOPENTENE ANNULATION
DANHEISER, RL
论文数:
0
引用数:
0
h-index:
0
DANHEISER, RL
CARINI, DJ
论文数:
0
引用数:
0
h-index:
0
CARINI, DJ
FINK, DM
论文数:
0
引用数:
0
h-index:
0
FINK, DM
BASAK, A
论文数:
0
引用数:
0
h-index:
0
BASAK, A
[J].
TETRAHEDRON,
1983,
39
(06)
: 935
-
947
[13]
ASYMMETRIC DIELS-ALDER REACTIONS - (S)-(+)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH=CH2] AS A CHIRAL ACRYLATE DIENOPHILE EQUIVALENT
DAVIES, SG
论文数:
0
引用数:
0
h-index:
0
DAVIES, SG
WALKER, JC
论文数:
0
引用数:
0
h-index:
0
WALKER, JC
[J].
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS,
1986,
(08)
: 609
-
610
[14]
SNCL4(4-TERT-BUC6H4CHO)2 - X-RAY CRYSTAL-STRUCTURE, SOLUTION NMR, AND IMPLICATIONS FOR REACTIONS AT COMPLEXED CARBONYLS
DENMARK, SE
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HENKE, BR
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0
h-index:
0
HENKE, BR
WEBER, E
论文数:
0
引用数:
0
h-index:
0
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[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
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(08)
: 2512
-
2514
[15]
STEREOCHEMICAL AND SPECTROSCOPIC STUDIES ON THE REACTION OF ALLYLSTANNANES WITH ALDEHYDES
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WEBER, EJ
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WILSON, TM
WILLSON, TM
论文数:
0
引用数:
0
h-index:
0
WILLSON, TM
[J].
TETRAHEDRON,
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45
(04)
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-
1065
[16]
ON THE LEWIS ACID-INDUCED ADDITION OF ALLYLSTANNANES TO ALDEHYDES - A SPECTROSCOPIC INVESTIGATION
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WILSON, T
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h-index:
0
WILSON, T
WILLSON, TM
论文数:
0
引用数:
0
h-index:
0
WILLSON, TM
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1988,
110
(03)
: 984
-
986
[17]
STEREOSPECIFIC CYCLOPROPANE SYNTHESIS FROM GAMMA-STANNYL ALCOHOLS
FLEMING, I
论文数:
0
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0
h-index:
0
FLEMING, I
URCH, CJ
论文数:
0
引用数:
0
h-index:
0
URCH, CJ
[J].
TETRAHEDRON LETTERS,
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24
(42)
: 4591
-
4594
[18]
A ONE-POT CONVERSION OF THE PHENYLDIMETHYLSILYL GROUP INTO A HYDROXYL GROUP
FLEMING, I
论文数:
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0
FLEMING, I
SANDERSON, PEJ
论文数:
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引用数:
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[J].
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UNIV LIBRE BRUSSEL,FAC SCI,COLL CHIM ORG PHYS,BRUSSEL 1050,BELGIUM
GIELEN, M
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6
(06)
: 198
-
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[20]
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0
引用数:
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h-index:
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机构:
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UNIV CAMERINO,INST PHARM & ORG CHEM,I-62032 CAMERINO,ITALY
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ANGELI, P
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h-index:
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机构:
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UNIV CAMERINO,INST PHARM & ORG CHEM,I-62032 CAMERINO,ITALY
ANGELI, P
GIANNELLA, M
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CAMERINO,INST PHARM & ORG CHEM,I-62032 CAMERINO,ITALY
UNIV CAMERINO,INST PHARM & ORG CHEM,I-62032 CAMERINO,ITALY
GIANNELLA, M
MELCHIORRE, C
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CAMERINO,INST PHARM & ORG CHEM,I-62032 CAMERINO,ITALY
UNIV CAMERINO,INST PHARM & ORG CHEM,I-62032 CAMERINO,ITALY
MELCHIORRE, C
[J].
SYNTHETIC COMMUNICATIONS,
1976,
6
(02)
: 63
-
68
←
1
2
3
4
5
6
7
→
共 69 条
[11]
CHEMISTRY OF DICARBONYL ETA-5-CYCLOPENTADIENYL-ETA-1-ALLYLIRON AND ETA-2-OLEFINIRON COMPLEXES - PREPARATION AND CYCLOADDITION REACTIONS
CUTLER, A
论文数:
0
引用数:
0
h-index:
0
机构:
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
CUTLER, A
EHNTHOLT, D
论文数:
0
引用数:
0
h-index:
0
机构:
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
EHNTHOLT, D
GIERING, WP
论文数:
0
引用数:
0
h-index:
0
机构:
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
GIERING, WP
LENNON, P
论文数:
0
引用数:
0
h-index:
0
机构:
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
LENNON, P
RAGHU, S
论文数:
0
引用数:
0
h-index:
0
机构:
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
RAGHU, S
ROSAN, A
论文数:
0
引用数:
0
h-index:
0
机构:
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
ROSAN, A
ROSENBLUM, M
论文数:
0
引用数:
0
h-index:
0
机构:
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
ROSENBLUM, M
TANCREDE, J
论文数:
0
引用数:
0
h-index:
0
机构:
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
TANCREDE, J
WELLS, D
论文数:
0
引用数:
0
h-index:
0
机构:
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
BRANDEIS UNIV,DEPT CHEM,WALTHAM,MA 02154
WELLS, D
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1976,
98
(12)
: 3495
-
3507
[12]
SCOPE AND STEREOCHEMICAL COURSE OF THE (TRIMETHYLSILYL)CYCLOPENTENE ANNULATION
DANHEISER, RL
论文数:
0
引用数:
0
h-index:
0
DANHEISER, RL
CARINI, DJ
论文数:
0
引用数:
0
h-index:
0
CARINI, DJ
FINK, DM
论文数:
0
引用数:
0
h-index:
0
FINK, DM
BASAK, A
论文数:
0
引用数:
0
h-index:
0
BASAK, A
[J].
TETRAHEDRON,
1983,
39
(06)
: 935
-
947
[13]
ASYMMETRIC DIELS-ALDER REACTIONS - (S)-(+)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH=CH2] AS A CHIRAL ACRYLATE DIENOPHILE EQUIVALENT
DAVIES, SG
论文数:
0
引用数:
0
h-index:
0
DAVIES, SG
WALKER, JC
论文数:
0
引用数:
0
h-index:
0
WALKER, JC
[J].
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS,
1986,
(08)
: 609
-
610
[14]
SNCL4(4-TERT-BUC6H4CHO)2 - X-RAY CRYSTAL-STRUCTURE, SOLUTION NMR, AND IMPLICATIONS FOR REACTIONS AT COMPLEXED CARBONYLS
DENMARK, SE
论文数:
0
引用数:
0
h-index:
0
DENMARK, SE
HENKE, BR
论文数:
0
引用数:
0
h-index:
0
HENKE, BR
WEBER, E
论文数:
0
引用数:
0
h-index:
0
WEBER, E
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1987,
109
(08)
: 2512
-
2514
[15]
STEREOCHEMICAL AND SPECTROSCOPIC STUDIES ON THE REACTION OF ALLYLSTANNANES WITH ALDEHYDES
DENMARK, SE
论文数:
0
引用数:
0
h-index:
0
DENMARK, SE
WEBER, EJ
论文数:
0
引用数:
0
h-index:
0
WEBER, EJ
WILSON, TM
论文数:
0
引用数:
0
h-index:
0
WILSON, TM
WILLSON, TM
论文数:
0
引用数:
0
h-index:
0
WILLSON, TM
[J].
TETRAHEDRON,
1989,
45
(04)
: 1053
-
1065
[16]
ON THE LEWIS ACID-INDUCED ADDITION OF ALLYLSTANNANES TO ALDEHYDES - A SPECTROSCOPIC INVESTIGATION
DENMARK, SE
论文数:
0
引用数:
0
h-index:
0
DENMARK, SE
WILSON, T
论文数:
0
引用数:
0
h-index:
0
WILSON, T
WILLSON, TM
论文数:
0
引用数:
0
h-index:
0
WILLSON, TM
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1988,
110
(03)
: 984
-
986
[17]
STEREOSPECIFIC CYCLOPROPANE SYNTHESIS FROM GAMMA-STANNYL ALCOHOLS
FLEMING, I
论文数:
0
引用数:
0
h-index:
0
FLEMING, I
URCH, CJ
论文数:
0
引用数:
0
h-index:
0
URCH, CJ
[J].
TETRAHEDRON LETTERS,
1983,
24
(42)
: 4591
-
4594
[18]
A ONE-POT CONVERSION OF THE PHENYLDIMETHYLSILYL GROUP INTO A HYDROXYL GROUP
FLEMING, I
论文数:
0
引用数:
0
h-index:
0
FLEMING, I
SANDERSON, PEJ
论文数:
0
引用数:
0
h-index:
0
SANDERSON, PEJ
[J].
TETRAHEDRON LETTERS,
1987,
28
(36)
: 4229
-
4232
[19]
FROM KINETICS TO SYNTHESIS OF CHIRAL TETRAORGANOTIN COMPOUNDS
GIELEN, M
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV LIBRE BRUSSEL,FAC SCI,COLL CHIM ORG PHYS,BRUSSEL 1050,BELGIUM
UNIV LIBRE BRUSSEL,FAC SCI,COLL CHIM ORG PHYS,BRUSSEL 1050,BELGIUM
GIELEN, M
[J].
ACCOUNTS OF CHEMICAL RESEARCH,
1973,
6
(06)
: 198
-
202
[20]
CHOLINERGIC COMPOUNDS .6. SYNTHESIS OF EPIALLO-DESETHERMUSCARINE
GUALTIERI, F
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CAMERINO,INST PHARM & ORG CHEM,I-62032 CAMERINO,ITALY
UNIV CAMERINO,INST PHARM & ORG CHEM,I-62032 CAMERINO,ITALY
GUALTIERI, F
ANGELI, P
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CAMERINO,INST PHARM & ORG CHEM,I-62032 CAMERINO,ITALY
UNIV CAMERINO,INST PHARM & ORG CHEM,I-62032 CAMERINO,ITALY
ANGELI, P
GIANNELLA, M
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CAMERINO,INST PHARM & ORG CHEM,I-62032 CAMERINO,ITALY
UNIV CAMERINO,INST PHARM & ORG CHEM,I-62032 CAMERINO,ITALY
GIANNELLA, M
MELCHIORRE, C
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CAMERINO,INST PHARM & ORG CHEM,I-62032 CAMERINO,ITALY
UNIV CAMERINO,INST PHARM & ORG CHEM,I-62032 CAMERINO,ITALY
MELCHIORRE, C
[J].
SYNTHETIC COMMUNICATIONS,
1976,
6
(02)
: 63
-
68
←
1
2
3
4
5
6
7
→