学术探索
学术期刊
新闻热点
数据分析
智能评审
立即登录
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
[11]
The SAMP-/RAMP-hydrazone methodology in asymmetric synthesis
Job, A
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH, Inst Organ Chem, D-52074 Aachen, Germany
Job, A
Janeck, CF
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH, Inst Organ Chem, D-52074 Aachen, Germany
Janeck, CF
Bettray, W
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH, Inst Organ Chem, D-52074 Aachen, Germany
Bettray, W
Peters, R
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH, Inst Organ Chem, D-52074 Aachen, Germany
Peters, R
Enders, D
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH, Inst Organ Chem, D-52074 Aachen, Germany
Enders, D
[J].
TETRAHEDRON,
2002,
58
(12)
: 2253
-
+
[12]
Meyers A. I., 1983, ASYMMETRIC SYNTHESIS, V3, P213
[13]
STANNOUS TRIFLATE MEDIATED ALDOL REACTION OF 3-ACYLTHIAZOLIDINE-2-THIONE - A CONVENIENT METHOD FOR THE STEREOSELECTIVE SYNTHESES OF BETA-HYDROXY ALDEHYDE AND BETA-HYDROXY CARBOXYLIC-ACID DERIVATIVES
MUKAIYAMA, T
论文数:
0
引用数:
0
h-index:
0
MUKAIYAMA, T
IWASAWA, N
论文数:
0
引用数:
0
h-index:
0
IWASAWA, N
[J].
CHEMISTRY LETTERS,
1982,
(12)
: 1903
-
1906
[14]
Pseudoephedrine as a practical chiral auxiliary for the synthesis of highly enantiomerically enriched carboxylic acids, alcohols, aldehydes, and ketones
Myers, AG
论文数:
0
引用数:
0
h-index:
0
机构:
Div. of Chem. and Chem. Engineering, California Institute of Technology, Pasadena
Myers, AG
Yang, BH
论文数:
0
引用数:
0
h-index:
0
机构:
Div. of Chem. and Chem. Engineering, California Institute of Technology, Pasadena
Yang, BH
Chen, H
论文数:
0
引用数:
0
h-index:
0
机构:
Div. of Chem. and Chem. Engineering, California Institute of Technology, Pasadena
Chen, H
McKinstry, L
论文数:
0
引用数:
0
h-index:
0
机构:
Div. of Chem. and Chem. Engineering, California Institute of Technology, Pasadena
McKinstry, L
Kopecky, DJ
论文数:
0
引用数:
0
h-index:
0
机构:
Div. of Chem. and Chem. Engineering, California Institute of Technology, Pasadena
Kopecky, DJ
Gleason, JL
论文数:
0
引用数:
0
h-index:
0
机构:
Div. of Chem. and Chem. Engineering, California Institute of Technology, Pasadena
Gleason, JL
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1997,
119
(28)
: 6496
-
6511
[15]
ASYMMETRIC ALKYLATION OF NORMAL-ACYLSULTAMS - A GENERAL-ROUTE TO ENANTIOMERICALLY PURE, CRYSTALLINE C(ALPHA,ALPHA)-DISUBSTITUTED CARBOXYLIC-ACID DERIVATIVES
OPPOLZER, W
论文数:
0
引用数:
0
h-index:
0
OPPOLZER, W
MORETTI, R
论文数:
0
引用数:
0
h-index:
0
MORETTI, R
THOMI, S
论文数:
0
引用数:
0
h-index:
0
THOMI, S
[J].
TETRAHEDRON LETTERS,
1989,
30
(41)
: 5603
-
5606
[16]
Superacidity and superelectrophilicity of BF3-carbonyl complexes
Ren, JH
论文数:
0
引用数:
0
h-index:
0
机构:
Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
Ren, JH
Cramer, CJ
论文数:
0
引用数:
0
h-index:
0
机构:
Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
Cramer, CJ
Squires, RR
论文数:
0
引用数:
0
h-index:
0
机构:
Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
Squires, RR
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1999,
121
(11)
: 2633
-
2634
[17]
Versatile asymmetric synthesis of the kavalactones: First synthesis of (+)-kavain
Smith, TE
论文数:
0
引用数:
0
h-index:
0
机构:
Williams Coll, Dept Chem, Williamstown, MA 01267 USA
Williams Coll, Dept Chem, Williamstown, MA 01267 USA
Smith, TE
Djang, M
论文数:
0
引用数:
0
h-index:
0
机构:
Williams Coll, Dept Chem, Williamstown, MA 01267 USA
Williams Coll, Dept Chem, Williamstown, MA 01267 USA
Djang, M
Velander, AJ
论文数:
0
引用数:
0
h-index:
0
机构:
Williams Coll, Dept Chem, Williamstown, MA 01267 USA
Williams Coll, Dept Chem, Williamstown, MA 01267 USA
Velander, AJ
Downey, CW
论文数:
0
引用数:
0
h-index:
0
机构:
Williams Coll, Dept Chem, Williamstown, MA 01267 USA
Williams Coll, Dept Chem, Williamstown, MA 01267 USA
Downey, CW
Carroll, KA
论文数:
0
引用数:
0
h-index:
0
机构:
Williams Coll, Dept Chem, Williamstown, MA 01267 USA
Williams Coll, Dept Chem, Williamstown, MA 01267 USA
Carroll, KA
van Alphen, S
论文数:
0
引用数:
0
h-index:
0
机构:
Williams Coll, Dept Chem, Williamstown, MA 01267 USA
Williams Coll, Dept Chem, Williamstown, MA 01267 USA
van Alphen, S
[J].
ORGANIC LETTERS,
2004,
6
(14)
: 2317
-
2320
[18]
Preparation, crystal structure analysis, and catalytic application of [(S)-BINAP]Ni(COD) and [(S)-BINAP]NiBr2
Spielvogel, DJ
论文数:
0
引用数:
0
h-index:
0
机构:
MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
Spielvogel, DJ
Davis, WM
论文数:
0
引用数:
0
h-index:
0
机构:
MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
Davis, WM
Buchwald, SL
论文数:
0
引用数:
0
h-index:
0
机构:
MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
Buchwald, SL
[J].
ORGANOMETALLICS,
2002,
21
(18)
: 3833
-
3836
←
1
2
→
共 18 条
[11]
The SAMP-/RAMP-hydrazone methodology in asymmetric synthesis
Job, A
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH, Inst Organ Chem, D-52074 Aachen, Germany
Job, A
Janeck, CF
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH, Inst Organ Chem, D-52074 Aachen, Germany
Janeck, CF
Bettray, W
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH, Inst Organ Chem, D-52074 Aachen, Germany
Bettray, W
Peters, R
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH, Inst Organ Chem, D-52074 Aachen, Germany
Peters, R
Enders, D
论文数:
0
引用数:
0
h-index:
0
机构:
Rhein Westfal TH, Inst Organ Chem, D-52074 Aachen, Germany
Rhein Westfal TH, Inst Organ Chem, D-52074 Aachen, Germany
Enders, D
[J].
TETRAHEDRON,
2002,
58
(12)
: 2253
-
+
[12]
Meyers A. I., 1983, ASYMMETRIC SYNTHESIS, V3, P213
[13]
STANNOUS TRIFLATE MEDIATED ALDOL REACTION OF 3-ACYLTHIAZOLIDINE-2-THIONE - A CONVENIENT METHOD FOR THE STEREOSELECTIVE SYNTHESES OF BETA-HYDROXY ALDEHYDE AND BETA-HYDROXY CARBOXYLIC-ACID DERIVATIVES
MUKAIYAMA, T
论文数:
0
引用数:
0
h-index:
0
MUKAIYAMA, T
IWASAWA, N
论文数:
0
引用数:
0
h-index:
0
IWASAWA, N
[J].
CHEMISTRY LETTERS,
1982,
(12)
: 1903
-
1906
[14]
Pseudoephedrine as a practical chiral auxiliary for the synthesis of highly enantiomerically enriched carboxylic acids, alcohols, aldehydes, and ketones
Myers, AG
论文数:
0
引用数:
0
h-index:
0
机构:
Div. of Chem. and Chem. Engineering, California Institute of Technology, Pasadena
Myers, AG
Yang, BH
论文数:
0
引用数:
0
h-index:
0
机构:
Div. of Chem. and Chem. Engineering, California Institute of Technology, Pasadena
Yang, BH
Chen, H
论文数:
0
引用数:
0
h-index:
0
机构:
Div. of Chem. and Chem. Engineering, California Institute of Technology, Pasadena
Chen, H
McKinstry, L
论文数:
0
引用数:
0
h-index:
0
机构:
Div. of Chem. and Chem. Engineering, California Institute of Technology, Pasadena
McKinstry, L
Kopecky, DJ
论文数:
0
引用数:
0
h-index:
0
机构:
Div. of Chem. and Chem. Engineering, California Institute of Technology, Pasadena
Kopecky, DJ
Gleason, JL
论文数:
0
引用数:
0
h-index:
0
机构:
Div. of Chem. and Chem. Engineering, California Institute of Technology, Pasadena
Gleason, JL
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1997,
119
(28)
: 6496
-
6511
[15]
ASYMMETRIC ALKYLATION OF NORMAL-ACYLSULTAMS - A GENERAL-ROUTE TO ENANTIOMERICALLY PURE, CRYSTALLINE C(ALPHA,ALPHA)-DISUBSTITUTED CARBOXYLIC-ACID DERIVATIVES
OPPOLZER, W
论文数:
0
引用数:
0
h-index:
0
OPPOLZER, W
MORETTI, R
论文数:
0
引用数:
0
h-index:
0
MORETTI, R
THOMI, S
论文数:
0
引用数:
0
h-index:
0
THOMI, S
[J].
TETRAHEDRON LETTERS,
1989,
30
(41)
: 5603
-
5606
[16]
Superacidity and superelectrophilicity of BF3-carbonyl complexes
Ren, JH
论文数:
0
引用数:
0
h-index:
0
机构:
Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
Ren, JH
Cramer, CJ
论文数:
0
引用数:
0
h-index:
0
机构:
Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
Cramer, CJ
Squires, RR
论文数:
0
引用数:
0
h-index:
0
机构:
Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
Squires, RR
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1999,
121
(11)
: 2633
-
2634
[17]
Versatile asymmetric synthesis of the kavalactones: First synthesis of (+)-kavain
Smith, TE
论文数:
0
引用数:
0
h-index:
0
机构:
Williams Coll, Dept Chem, Williamstown, MA 01267 USA
Williams Coll, Dept Chem, Williamstown, MA 01267 USA
Smith, TE
Djang, M
论文数:
0
引用数:
0
h-index:
0
机构:
Williams Coll, Dept Chem, Williamstown, MA 01267 USA
Williams Coll, Dept Chem, Williamstown, MA 01267 USA
Djang, M
Velander, AJ
论文数:
0
引用数:
0
h-index:
0
机构:
Williams Coll, Dept Chem, Williamstown, MA 01267 USA
Williams Coll, Dept Chem, Williamstown, MA 01267 USA
Velander, AJ
Downey, CW
论文数:
0
引用数:
0
h-index:
0
机构:
Williams Coll, Dept Chem, Williamstown, MA 01267 USA
Williams Coll, Dept Chem, Williamstown, MA 01267 USA
Downey, CW
Carroll, KA
论文数:
0
引用数:
0
h-index:
0
机构:
Williams Coll, Dept Chem, Williamstown, MA 01267 USA
Williams Coll, Dept Chem, Williamstown, MA 01267 USA
Carroll, KA
van Alphen, S
论文数:
0
引用数:
0
h-index:
0
机构:
Williams Coll, Dept Chem, Williamstown, MA 01267 USA
Williams Coll, Dept Chem, Williamstown, MA 01267 USA
van Alphen, S
[J].
ORGANIC LETTERS,
2004,
6
(14)
: 2317
-
2320
[18]
Preparation, crystal structure analysis, and catalytic application of [(S)-BINAP]Ni(COD) and [(S)-BINAP]NiBr2
Spielvogel, DJ
论文数:
0
引用数:
0
h-index:
0
机构:
MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
Spielvogel, DJ
Davis, WM
论文数:
0
引用数:
0
h-index:
0
机构:
MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
Davis, WM
Buchwald, SL
论文数:
0
引用数:
0
h-index:
0
机构:
MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
Buchwald, SL
[J].
ORGANOMETALLICS,
2002,
21
(18)
: 3833
-
3836
←
1
2
→