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STEREOCHEMISTRY OF CUPRATE ADDITION TO 4-ALKYLCYCLOHEPTENONES, 5-ALKYLCYCLOHEPTENONES, AND 6-ALKYLCYCLOHEPTENONES
被引:25
作者
:
HEATHCOCK, CH
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, University of California, Berkeley
HEATHCOCK, CH
GERMROTH, TC
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, University of California, Berkeley
GERMROTH, TC
GRAHAM, SL
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, University of California, Berkeley
GRAHAM, SL
机构
:
[1]
Department of Chemistry, University of California, Berkeley
来源
:
JOURNAL OF ORGANIC CHEMISTRY
|
1979年
/ 44卷
/ 25期
关键词
:
D O I
:
10.1021/jo00393a004
中图分类号
:
O62 [有机化学];
学科分类号
:
070303 ;
081704 ;
摘要
:
The reactions of cycloheptenones 1-7 with Me2CuLi and (f-Bu)2CuLi have been studied. Stereostructures of the resulting diastereomeric products have been determined by comparison with known compounds, by unambiguous synthesis, or by the use of 13C NMR spectroscopy. Good stereoselectivity is observed in the reaction of Me2CuLi with enones 2, 4, and 7 and in the reaction of (f-Bu)2CuLi with enones 1, 5, and 6. © 1979, American Chemical Society. All rights reserved.
引用
收藏
页码:4481 / 4487
页数:7
相关论文
共 17 条
[1]
REGIOSPECIFIC ALKYLATION OF ENOLATE IONS IN LIQUID AMMONIA-TETRAHYDROFURAN
BINKLEY, ES
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CALIF,DEPT CHEM,BERKELEY,CA 94720
UNIV CALIF,DEPT CHEM,BERKELEY,CA 94720
BINKLEY, ES
HEATHCOCK, CH
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CALIF,DEPT CHEM,BERKELEY,CA 94720
UNIV CALIF,DEPT CHEM,BERKELEY,CA 94720
HEATHCOCK, CH
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1975,
40
(15)
: 2156
-
2160
[2]
PHOTOISOMERIZATION OF CONJUGATED CYCLOPROPYL KETONES
DAUBEN, WG
论文数:
0
引用数:
0
h-index:
0
DAUBEN, WG
SHAFFER, GW
论文数:
0
引用数:
0
h-index:
0
SHAFFER, GW
DEVINY, EJ
论文数:
0
引用数:
0
h-index:
0
DEVINY, EJ
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1970,
92
(21)
: 6273
-
&
[3]
CYCLOALK-2-ENONES AND ALPHA,BETA,ALPHA',BETA'-CYCLOALKADIENONES .A. SYNTHESIS .B. ON DIRECTION OF BROMINATION OF 2-SUBSTITUTED CYCLOALKANONES AND THEIR KETALS
GARBISCH, EW
论文数:
0
引用数:
0
h-index:
0
GARBISCH, EW
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1965,
30
(07)
: 2109
-
&
[4]
STEREOSPECIFIC SYNTHESES OF 7 DIMETHYLCYCLOHEPTANES
HENDRICKSON, JB
论文数:
0
引用数:
0
h-index:
0
HENDRICKSON, JB
BOECKMAN, RK
论文数:
0
引用数:
0
h-index:
0
BOECKMAN, RK
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1971,
36
(16)
: 2315
-
+
[5]
REACTIONS INVOLVING ELECTRON-TRANSFER .12. EFFECTS OF SOLVENT AND SUBSTITUENTS UPON ABILITY OF LITHIUM DIORGANOCUPRATES TO ADD TO ENONES
HOUSE, HO
论文数:
0
引用数:
0
h-index:
0
HOUSE, HO
WILKINS, JM
论文数:
0
引用数:
0
h-index:
0
WILKINS, JM
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1978,
43
(12)
: 2443
-
2454
[6]
REACTION OF 1-SILYLOXYBICYCLO[N.1.0]ALKANES WITH FEIIICL-3 - FACILE SYNTHESIS OF 2-CYCLOALKENONES VIA RING ENLARGEMENT OF CYCLIC KETONES
ITO, Y
论文数:
0
引用数:
0
h-index:
0
机构:
KYOTO UNIV,DEPT SYNTH CHEM,KYOTO,JAPAN
KYOTO UNIV,DEPT SYNTH CHEM,KYOTO,JAPAN
ITO, Y
FUJII, S
论文数:
0
引用数:
0
h-index:
0
机构:
KYOTO UNIV,DEPT SYNTH CHEM,KYOTO,JAPAN
KYOTO UNIV,DEPT SYNTH CHEM,KYOTO,JAPAN
FUJII, S
SAEGUSA, T
论文数:
0
引用数:
0
h-index:
0
机构:
KYOTO UNIV,DEPT SYNTH CHEM,KYOTO,JAPAN
KYOTO UNIV,DEPT SYNTH CHEM,KYOTO,JAPAN
SAEGUSA, T
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1976,
41
(11)
: 2073
-
2074
[7]
TETRAKIS[IODO(TRI-NORMAL-BUTYLPHOSPHINE)-COPPER(I)] AND IODO-(2,2'-BIPYRIDINE)-(TRI-NORMAL-BUTYLPHOSPHINE)COPPER(I)
KAUFFMAN, GB
论文数:
0
引用数:
0
h-index:
0
KAUFFMAN, GB
TETER, LA
论文数:
0
引用数:
0
h-index:
0
TETER, LA
[J].
INORGANIC SYNTHESES,
1963,
7
: 9
-
12
[8]
Spectroscopic evidence for conjugation in cyclopropane systems
Klotz, IM
论文数:
0
引用数:
0
h-index:
0
机构:
Northwestern Univ, Chem Lab, Evanston, IL USA
Northwestern Univ, Chem Lab, Evanston, IL USA
Klotz, IM
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1944,
66
: 88
-
91
[9]
SYNTHESIS OF 1-HYDROXYBICYCLO[N.1.0]ALKANES FROM SILYL ALKENYL ETHERS - NOVEL CLASS OF CYCLOPROPANOLS
MURAI, S
论文数:
0
引用数:
0
h-index:
0
机构:
OSAKA UNIV,FAC ENGN,DEPT PETR CHEM,SUITA,OSAKA,JAPAN
OSAKA UNIV,FAC ENGN,DEPT PETR CHEM,SUITA,OSAKA,JAPAN
MURAI, S
AYA, T
论文数:
0
引用数:
0
h-index:
0
机构:
OSAKA UNIV,FAC ENGN,DEPT PETR CHEM,SUITA,OSAKA,JAPAN
OSAKA UNIV,FAC ENGN,DEPT PETR CHEM,SUITA,OSAKA,JAPAN
AYA, T
SONODA, N
论文数:
0
引用数:
0
h-index:
0
机构:
OSAKA UNIV,FAC ENGN,DEPT PETR CHEM,SUITA,OSAKA,JAPAN
OSAKA UNIV,FAC ENGN,DEPT PETR CHEM,SUITA,OSAKA,JAPAN
SONODA, N
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1973,
38
(25)
: 4354
-
4356
[10]
NGOC TLT, 1968, CR ACAD SCI C CHIM, V267, P776
←
1
2
→
共 17 条
[1]
REGIOSPECIFIC ALKYLATION OF ENOLATE IONS IN LIQUID AMMONIA-TETRAHYDROFURAN
BINKLEY, ES
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CALIF,DEPT CHEM,BERKELEY,CA 94720
UNIV CALIF,DEPT CHEM,BERKELEY,CA 94720
BINKLEY, ES
HEATHCOCK, CH
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CALIF,DEPT CHEM,BERKELEY,CA 94720
UNIV CALIF,DEPT CHEM,BERKELEY,CA 94720
HEATHCOCK, CH
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1975,
40
(15)
: 2156
-
2160
[2]
PHOTOISOMERIZATION OF CONJUGATED CYCLOPROPYL KETONES
DAUBEN, WG
论文数:
0
引用数:
0
h-index:
0
DAUBEN, WG
SHAFFER, GW
论文数:
0
引用数:
0
h-index:
0
SHAFFER, GW
DEVINY, EJ
论文数:
0
引用数:
0
h-index:
0
DEVINY, EJ
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1970,
92
(21)
: 6273
-
&
[3]
CYCLOALK-2-ENONES AND ALPHA,BETA,ALPHA',BETA'-CYCLOALKADIENONES .A. SYNTHESIS .B. ON DIRECTION OF BROMINATION OF 2-SUBSTITUTED CYCLOALKANONES AND THEIR KETALS
GARBISCH, EW
论文数:
0
引用数:
0
h-index:
0
GARBISCH, EW
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1965,
30
(07)
: 2109
-
&
[4]
STEREOSPECIFIC SYNTHESES OF 7 DIMETHYLCYCLOHEPTANES
HENDRICKSON, JB
论文数:
0
引用数:
0
h-index:
0
HENDRICKSON, JB
BOECKMAN, RK
论文数:
0
引用数:
0
h-index:
0
BOECKMAN, RK
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1971,
36
(16)
: 2315
-
+
[5]
REACTIONS INVOLVING ELECTRON-TRANSFER .12. EFFECTS OF SOLVENT AND SUBSTITUENTS UPON ABILITY OF LITHIUM DIORGANOCUPRATES TO ADD TO ENONES
HOUSE, HO
论文数:
0
引用数:
0
h-index:
0
HOUSE, HO
WILKINS, JM
论文数:
0
引用数:
0
h-index:
0
WILKINS, JM
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1978,
43
(12)
: 2443
-
2454
[6]
REACTION OF 1-SILYLOXYBICYCLO[N.1.0]ALKANES WITH FEIIICL-3 - FACILE SYNTHESIS OF 2-CYCLOALKENONES VIA RING ENLARGEMENT OF CYCLIC KETONES
ITO, Y
论文数:
0
引用数:
0
h-index:
0
机构:
KYOTO UNIV,DEPT SYNTH CHEM,KYOTO,JAPAN
KYOTO UNIV,DEPT SYNTH CHEM,KYOTO,JAPAN
ITO, Y
FUJII, S
论文数:
0
引用数:
0
h-index:
0
机构:
KYOTO UNIV,DEPT SYNTH CHEM,KYOTO,JAPAN
KYOTO UNIV,DEPT SYNTH CHEM,KYOTO,JAPAN
FUJII, S
SAEGUSA, T
论文数:
0
引用数:
0
h-index:
0
机构:
KYOTO UNIV,DEPT SYNTH CHEM,KYOTO,JAPAN
KYOTO UNIV,DEPT SYNTH CHEM,KYOTO,JAPAN
SAEGUSA, T
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1976,
41
(11)
: 2073
-
2074
[7]
TETRAKIS[IODO(TRI-NORMAL-BUTYLPHOSPHINE)-COPPER(I)] AND IODO-(2,2'-BIPYRIDINE)-(TRI-NORMAL-BUTYLPHOSPHINE)COPPER(I)
KAUFFMAN, GB
论文数:
0
引用数:
0
h-index:
0
KAUFFMAN, GB
TETER, LA
论文数:
0
引用数:
0
h-index:
0
TETER, LA
[J].
INORGANIC SYNTHESES,
1963,
7
: 9
-
12
[8]
Spectroscopic evidence for conjugation in cyclopropane systems
Klotz, IM
论文数:
0
引用数:
0
h-index:
0
机构:
Northwestern Univ, Chem Lab, Evanston, IL USA
Northwestern Univ, Chem Lab, Evanston, IL USA
Klotz, IM
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1944,
66
: 88
-
91
[9]
SYNTHESIS OF 1-HYDROXYBICYCLO[N.1.0]ALKANES FROM SILYL ALKENYL ETHERS - NOVEL CLASS OF CYCLOPROPANOLS
MURAI, S
论文数:
0
引用数:
0
h-index:
0
机构:
OSAKA UNIV,FAC ENGN,DEPT PETR CHEM,SUITA,OSAKA,JAPAN
OSAKA UNIV,FAC ENGN,DEPT PETR CHEM,SUITA,OSAKA,JAPAN
MURAI, S
AYA, T
论文数:
0
引用数:
0
h-index:
0
机构:
OSAKA UNIV,FAC ENGN,DEPT PETR CHEM,SUITA,OSAKA,JAPAN
OSAKA UNIV,FAC ENGN,DEPT PETR CHEM,SUITA,OSAKA,JAPAN
AYA, T
SONODA, N
论文数:
0
引用数:
0
h-index:
0
机构:
OSAKA UNIV,FAC ENGN,DEPT PETR CHEM,SUITA,OSAKA,JAPAN
OSAKA UNIV,FAC ENGN,DEPT PETR CHEM,SUITA,OSAKA,JAPAN
SONODA, N
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1973,
38
(25)
: 4354
-
4356
[10]
NGOC TLT, 1968, CR ACAD SCI C CHIM, V267, P776
←
1
2
→