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A study of asymmetric protonation with chiral beta-hydroxy sulfoxides. Asymmetric synthesis of (-)-epibatidine
被引:63
作者
:
Kosugi, H
论文数:
0
引用数:
0
h-index:
0
机构:
Inst. for Chemical Reaction Science, Tohoku University, Katahira, Aoba-ku
Kosugi, H
Abe, M
论文数:
0
引用数:
0
h-index:
0
机构:
Inst. for Chemical Reaction Science, Tohoku University, Katahira, Aoba-ku
Abe, M
Hatsuda, R
论文数:
0
引用数:
0
h-index:
0
机构:
Inst. for Chemical Reaction Science, Tohoku University, Katahira, Aoba-ku
Hatsuda, R
Uda, H
论文数:
0
引用数:
0
h-index:
0
机构:
Inst. for Chemical Reaction Science, Tohoku University, Katahira, Aoba-ku
Uda, H
Kato, M
论文数:
0
引用数:
0
h-index:
0
机构:
Inst. for Chemical Reaction Science, Tohoku University, Katahira, Aoba-ku
Kato, M
机构
:
[1]
Inst. for Chemical Reaction Science, Tohoku University, Katahira, Aoba-ku
来源
:
CHEMICAL COMMUNICATIONS
|
1997年
/ 19期
关键词
:
D O I
:
10.1039/a704779g
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
The asymmetric synthesis of (-)-epibatidine 1, employing as the key step the asymmetric protonation of the achiral lithum enolate of cyclohexanone derivative 5 with chiral beta-hydroxy sulfoxide 3b, is described.
引用
收藏
页码:1857 / 1858
页数:2
相关论文
共 29 条
[21]
SENOKUCHI K, 1994, SYNLETT, P343
[22]
SYNTHESIS OF EPIBATIDINE
SESTANJ, K
论文数:
0
引用数:
0
h-index:
0
机构:
Wyeth-Ayerst Research, Princeton
SESTANJ, K
MELENSKI, E
论文数:
0
引用数:
0
h-index:
0
机构:
Wyeth-Ayerst Research, Princeton
MELENSKI, E
JIRKOVSKY, I
论文数:
0
引用数:
0
h-index:
0
机构:
Wyeth-Ayerst Research, Princeton
JIRKOVSKY, I
[J].
TETRAHEDRON LETTERS,
1994,
35
(30)
: 5417
-
5420
[23]
EPIBATIDINE - A NOVEL (CHLOROPYRIDYL)AZABICYCLOHEPTANE WITH POTENT ANALGESIC ACTIVITY FROM AN ECUADORIAN POISON FROG
SPANDE, TF
论文数:
0
引用数:
0
h-index:
0
机构:
NIDDKD,ANALYT CHEM LAB,BETHESDA,MD 20892
SPANDE, TF
GARRAFFO, HM
论文数:
0
引用数:
0
h-index:
0
机构:
NIDDKD,ANALYT CHEM LAB,BETHESDA,MD 20892
GARRAFFO, HM
EDWARDS, MW
论文数:
0
引用数:
0
h-index:
0
机构:
NIDDKD,ANALYT CHEM LAB,BETHESDA,MD 20892
EDWARDS, MW
YEH, HJC
论文数:
0
引用数:
0
h-index:
0
机构:
NIDDKD,ANALYT CHEM LAB,BETHESDA,MD 20892
YEH, HJC
PANNELL, L
论文数:
0
引用数:
0
h-index:
0
机构:
NIDDKD,ANALYT CHEM LAB,BETHESDA,MD 20892
PANNELL, L
DALY, JW
论文数:
0
引用数:
0
h-index:
0
机构:
NIDDKD,ANALYT CHEM LAB,BETHESDA,MD 20892
DALY, JW
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1992,
114
(09)
: 3475
-
3478
[24]
STZANTAY C, 1994, TETRAHEDRON LETT, V35, P3171
[25]
An asymmetric synthesis (-)-epibatidine
Trost, BM
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Stanford University, Stanford
Trost, BM
Cook, GR
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Stanford University, Stanford
Cook, GR
[J].
TETRAHEDRON LETTERS,
1996,
37
(42)
: 7485
-
7488
[26]
ENANTIOMER-DIFFERENTIATION INDUCED BY AN ENANTIOMERIC EXCESS DURING CHROMATOGRAPHY WITH ACHIRAL PHASES
TSAI, WL
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
TSAI, WL
HERMANN, K
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
HERMANN, K
HUG, E
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
HUG, E
ROHDE, B
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
ROHDE, B
DREIDING, AS
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
DREIDING, AS
[J].
HELVETICA CHIMICA ACTA,
1985,
68
(08)
: 2238
-
2243
[27]
Total synthesis of (+/-) epibatidine
Xu, R
论文数:
0
引用数:
0
h-index:
0
机构:
Shanghai Institute of Materia Medica, Chinese Academy of Sciences
Xu, R
Chu, GH
论文数:
0
引用数:
0
h-index:
0
机构:
Shanghai Institute of Materia Medica, Chinese Academy of Sciences
Chu, GH
Bai, DL
论文数:
0
引用数:
0
h-index:
0
机构:
Shanghai Institute of Materia Medica, Chinese Academy of Sciences
Bai, DL
[J].
TETRAHEDRON LETTERS,
1996,
37
(09)
: 1463
-
1466
[28]
HIGHLY STEREOSELECTIVE ASYMMETRIC MICHAEL ADDITION-REACTIONS EMPLOYING (R-E)-3,3,3-TRIFLUOROPROP-1-ENYL PARA-TOLYL SULFOXIDE
YAMAZAKI, T
论文数:
0
引用数:
0
h-index:
0
YAMAZAKI, T
ISHIKAWA, N
论文数:
0
引用数:
0
h-index:
0
ISHIKAWA, N
IWATSUBO, H
论文数:
0
引用数:
0
h-index:
0
IWATSUBO, H
KITAZUME, T
论文数:
0
引用数:
0
h-index:
0
KITAZUME, T
[J].
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS,
1987,
(18)
: 1340
-
1342
[29]
A short and efficient total synthesis of (+/-)-epibatidine
Zhang, CM
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV NEW ORLEANS,DEPT CHEM,NEW ORLEANS,LA 70148
UNIV NEW ORLEANS,DEPT CHEM,NEW ORLEANS,LA 70148
Zhang, CM
Trudell, ML
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV NEW ORLEANS,DEPT CHEM,NEW ORLEANS,LA 70148
UNIV NEW ORLEANS,DEPT CHEM,NEW ORLEANS,LA 70148
Trudell, ML
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1996,
61
(20)
: 7189
-
7191
←
1
2
3
→
共 29 条
[21]
SENOKUCHI K, 1994, SYNLETT, P343
[22]
SYNTHESIS OF EPIBATIDINE
SESTANJ, K
论文数:
0
引用数:
0
h-index:
0
机构:
Wyeth-Ayerst Research, Princeton
SESTANJ, K
MELENSKI, E
论文数:
0
引用数:
0
h-index:
0
机构:
Wyeth-Ayerst Research, Princeton
MELENSKI, E
JIRKOVSKY, I
论文数:
0
引用数:
0
h-index:
0
机构:
Wyeth-Ayerst Research, Princeton
JIRKOVSKY, I
[J].
TETRAHEDRON LETTERS,
1994,
35
(30)
: 5417
-
5420
[23]
EPIBATIDINE - A NOVEL (CHLOROPYRIDYL)AZABICYCLOHEPTANE WITH POTENT ANALGESIC ACTIVITY FROM AN ECUADORIAN POISON FROG
SPANDE, TF
论文数:
0
引用数:
0
h-index:
0
机构:
NIDDKD,ANALYT CHEM LAB,BETHESDA,MD 20892
SPANDE, TF
GARRAFFO, HM
论文数:
0
引用数:
0
h-index:
0
机构:
NIDDKD,ANALYT CHEM LAB,BETHESDA,MD 20892
GARRAFFO, HM
EDWARDS, MW
论文数:
0
引用数:
0
h-index:
0
机构:
NIDDKD,ANALYT CHEM LAB,BETHESDA,MD 20892
EDWARDS, MW
YEH, HJC
论文数:
0
引用数:
0
h-index:
0
机构:
NIDDKD,ANALYT CHEM LAB,BETHESDA,MD 20892
YEH, HJC
PANNELL, L
论文数:
0
引用数:
0
h-index:
0
机构:
NIDDKD,ANALYT CHEM LAB,BETHESDA,MD 20892
PANNELL, L
DALY, JW
论文数:
0
引用数:
0
h-index:
0
机构:
NIDDKD,ANALYT CHEM LAB,BETHESDA,MD 20892
DALY, JW
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1992,
114
(09)
: 3475
-
3478
[24]
STZANTAY C, 1994, TETRAHEDRON LETT, V35, P3171
[25]
An asymmetric synthesis (-)-epibatidine
Trost, BM
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Stanford University, Stanford
Trost, BM
Cook, GR
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Stanford University, Stanford
Cook, GR
[J].
TETRAHEDRON LETTERS,
1996,
37
(42)
: 7485
-
7488
[26]
ENANTIOMER-DIFFERENTIATION INDUCED BY AN ENANTIOMERIC EXCESS DURING CHROMATOGRAPHY WITH ACHIRAL PHASES
TSAI, WL
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
TSAI, WL
HERMANN, K
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
HERMANN, K
HUG, E
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
HUG, E
ROHDE, B
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
ROHDE, B
DREIDING, AS
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
UNIV ZURICH,INST ORGAN CHEM,WINTERTHURERSTR 190,CH-8057 ZURICH,SWITZERLAND
DREIDING, AS
[J].
HELVETICA CHIMICA ACTA,
1985,
68
(08)
: 2238
-
2243
[27]
Total synthesis of (+/-) epibatidine
Xu, R
论文数:
0
引用数:
0
h-index:
0
机构:
Shanghai Institute of Materia Medica, Chinese Academy of Sciences
Xu, R
Chu, GH
论文数:
0
引用数:
0
h-index:
0
机构:
Shanghai Institute of Materia Medica, Chinese Academy of Sciences
Chu, GH
Bai, DL
论文数:
0
引用数:
0
h-index:
0
机构:
Shanghai Institute of Materia Medica, Chinese Academy of Sciences
Bai, DL
[J].
TETRAHEDRON LETTERS,
1996,
37
(09)
: 1463
-
1466
[28]
HIGHLY STEREOSELECTIVE ASYMMETRIC MICHAEL ADDITION-REACTIONS EMPLOYING (R-E)-3,3,3-TRIFLUOROPROP-1-ENYL PARA-TOLYL SULFOXIDE
YAMAZAKI, T
论文数:
0
引用数:
0
h-index:
0
YAMAZAKI, T
ISHIKAWA, N
论文数:
0
引用数:
0
h-index:
0
ISHIKAWA, N
IWATSUBO, H
论文数:
0
引用数:
0
h-index:
0
IWATSUBO, H
KITAZUME, T
论文数:
0
引用数:
0
h-index:
0
KITAZUME, T
[J].
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS,
1987,
(18)
: 1340
-
1342
[29]
A short and efficient total synthesis of (+/-)-epibatidine
Zhang, CM
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV NEW ORLEANS,DEPT CHEM,NEW ORLEANS,LA 70148
UNIV NEW ORLEANS,DEPT CHEM,NEW ORLEANS,LA 70148
Zhang, CM
Trudell, ML
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV NEW ORLEANS,DEPT CHEM,NEW ORLEANS,LA 70148
UNIV NEW ORLEANS,DEPT CHEM,NEW ORLEANS,LA 70148
Trudell, ML
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1996,
61
(20)
: 7189
-
7191
←
1
2
3
→