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Ni(II) Tol-BINAP-catalyzed enantioselective orthoester alkylations of N-acylthiazolidinethiones
被引:57
作者
:
Evans, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Evans, DA
[
1
]
Thomson, RJ
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Thomson, RJ
[
1
]
机构
:
[1]
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
来源
:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
|
2005年
/ 127卷
/ 30期
关键词
:
D O I
:
10.1021/ja053386s
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
The development of a Ni(II) (S)-Tol-BINAP-catalyzed enantioselective alkylation of N-acylthiazolidinethiones with trimethyl orthoformate is described. The reaction is general with respect to the thiazolidinethione, providing the desired adducts in good to excellent yield and with high levels of enantioselectivity (11 examples, 51-92% yield, 90-99% ee). The products are readily converted into a variety of synthetically useful derivatives in a straightforward manner. Copyright © 2005 American Chemical Society.
引用
收藏
页码:10506 / 10507
页数:2
相关论文
共 18 条
[1]
Asymmetric aldol additions:: Use of titanium tetrachloride and (-)-sparteine for the soft enolization of N-acyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones
Crimmins, MT
论文数:
0
引用数:
0
h-index:
0
机构:
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Crimmins, MT
King, BW
论文数:
0
引用数:
0
h-index:
0
机构:
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
King, BW
Tabet, EA
论文数:
0
引用数:
0
h-index:
0
机构:
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Tabet, EA
Chaudhary, K
论文数:
0
引用数:
0
h-index:
0
机构:
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Chaudhary, K
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2001,
66
(03)
: 894
-
902
[2]
Titanium enolates of thiazolidinethione chiral auxiliaries: Versatile tools for asymmetric aldol additions
Crimmins, MT
论文数:
0
引用数:
0
h-index:
0
机构:
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Crimmins, MT
Chaudhary, K
论文数:
0
引用数:
0
h-index:
0
机构:
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Chaudhary, K
[J].
ORGANIC LETTERS,
2000,
2
(06)
: 775
-
777
[3]
Enantioselective alkylations of tributyltin enolates catalyzed by Cr(salen)Cl: Access to enantiomerically enriched all-carbon quaternary centers
Doyle, AG
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Doyle, AG
Jacobsen, EN
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Jacobsen, EN
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005,
127
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-
63
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Evans D. A., 1983, ASYMMETRIC SYNTHESIS, V3, P83
[5]
NEW PROCEDURE FOR THE DIRECT GENERATION OF TITANIUM ENOLATES - DIASTEREOSELECTIVE BOND CONSTRUCTIONS WITH REPRESENTATIVE ELECTROPHILES
EVANS, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Massachusetts, 02138, Cambridge
EVANS, DA
URPI, F
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Massachusetts, 02138, Cambridge
URPI, F
SOMERS, TC
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Massachusetts, 02138, Cambridge
SOMERS, TC
CLARK, JS
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Massachusetts, 02138, Cambridge
CLARK, JS
BILODEAU, MT
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Massachusetts, 02138, Cambridge
BILODEAU, MT
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1990,
112
(22)
: 8215
-
8216
[6]
Ni(II) bis(oxazoline)-catalyzed enantioselective syn aldol reactions of N-propionylthiazolidinethiones in the presence of silyl triflates
Evans, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Evans, DA
Downey, CW
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Downey, CW
Hubbs, JL
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Hubbs, JL
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2003,
125
(29)
: 8706
-
8707
[7]
GENERAL-METHOD FOR THE SYNTHESIS OF ENOL ETHERS (VINYL ETHERS) FROM ACETALS
GASSMAN, PG
论文数:
0
引用数:
0
h-index:
0
GASSMAN, PG
BURNS, SJ
论文数:
0
引用数:
0
h-index:
0
BURNS, SJ
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1988,
53
(23)
: 5574
-
5576
[8]
PALLADIUM(II)-CATALYZED ASYMMETRIC ACETALIZATION OF ALKENES
HOSOKAWA, T
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Faculty of Engineering Science, Osaka University, Machikaneyama, Toyonaka
HOSOKAWA, T
YAMANAKA, T
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Faculty of Engineering Science, Osaka University, Machikaneyama, Toyonaka
YAMANAKA, T
ITOTANI, M
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Faculty of Engineering Science, Osaka University, Machikaneyama, Toyonaka
ITOTANI, M
MURAHASHI, SI
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Faculty of Engineering Science, Osaka University, Machikaneyama, Toyonaka
MURAHASHI, SI
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1995,
60
(19)
: 6159
-
6167
[9]
HUGHES DL, 1999, COMPREHENSIVE ASYMME, V3, P1273
[10]
HUGHES DL, 2004, COMPREHENSIVE ASYMME, V1, P161
←
1
2
→
共 18 条
[1]
Asymmetric aldol additions:: Use of titanium tetrachloride and (-)-sparteine for the soft enolization of N-acyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones
Crimmins, MT
论文数:
0
引用数:
0
h-index:
0
机构:
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Crimmins, MT
King, BW
论文数:
0
引用数:
0
h-index:
0
机构:
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
King, BW
Tabet, EA
论文数:
0
引用数:
0
h-index:
0
机构:
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Tabet, EA
Chaudhary, K
论文数:
0
引用数:
0
h-index:
0
机构:
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Chaudhary, K
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2001,
66
(03)
: 894
-
902
[2]
Titanium enolates of thiazolidinethione chiral auxiliaries: Versatile tools for asymmetric aldol additions
Crimmins, MT
论文数:
0
引用数:
0
h-index:
0
机构:
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Crimmins, MT
Chaudhary, K
论文数:
0
引用数:
0
h-index:
0
机构:
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA
Chaudhary, K
[J].
ORGANIC LETTERS,
2000,
2
(06)
: 775
-
777
[3]
Enantioselective alkylations of tributyltin enolates catalyzed by Cr(salen)Cl: Access to enantiomerically enriched all-carbon quaternary centers
Doyle, AG
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Doyle, AG
Jacobsen, EN
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Jacobsen, EN
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005,
127
(01)
: 62
-
63
[4]
Evans D. A., 1983, ASYMMETRIC SYNTHESIS, V3, P83
[5]
NEW PROCEDURE FOR THE DIRECT GENERATION OF TITANIUM ENOLATES - DIASTEREOSELECTIVE BOND CONSTRUCTIONS WITH REPRESENTATIVE ELECTROPHILES
EVANS, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Massachusetts, 02138, Cambridge
EVANS, DA
URPI, F
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Massachusetts, 02138, Cambridge
URPI, F
SOMERS, TC
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Massachusetts, 02138, Cambridge
SOMERS, TC
CLARK, JS
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Massachusetts, 02138, Cambridge
CLARK, JS
BILODEAU, MT
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Massachusetts, 02138, Cambridge
BILODEAU, MT
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1990,
112
(22)
: 8215
-
8216
[6]
Ni(II) bis(oxazoline)-catalyzed enantioselective syn aldol reactions of N-propionylthiazolidinethiones in the presence of silyl triflates
Evans, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Evans, DA
Downey, CW
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Downey, CW
Hubbs, JL
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Hubbs, JL
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2003,
125
(29)
: 8706
-
8707
[7]
GENERAL-METHOD FOR THE SYNTHESIS OF ENOL ETHERS (VINYL ETHERS) FROM ACETALS
GASSMAN, PG
论文数:
0
引用数:
0
h-index:
0
GASSMAN, PG
BURNS, SJ
论文数:
0
引用数:
0
h-index:
0
BURNS, SJ
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1988,
53
(23)
: 5574
-
5576
[8]
PALLADIUM(II)-CATALYZED ASYMMETRIC ACETALIZATION OF ALKENES
HOSOKAWA, T
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Faculty of Engineering Science, Osaka University, Machikaneyama, Toyonaka
HOSOKAWA, T
YAMANAKA, T
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Faculty of Engineering Science, Osaka University, Machikaneyama, Toyonaka
YAMANAKA, T
ITOTANI, M
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Faculty of Engineering Science, Osaka University, Machikaneyama, Toyonaka
ITOTANI, M
MURAHASHI, SI
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Faculty of Engineering Science, Osaka University, Machikaneyama, Toyonaka
MURAHASHI, SI
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1995,
60
(19)
: 6159
-
6167
[9]
HUGHES DL, 1999, COMPREHENSIVE ASYMME, V3, P1273
[10]
HUGHES DL, 2004, COMPREHENSIVE ASYMME, V1, P161
←
1
2
→