共 80 条
Enantioselective Lewis acid catalyzed Michael reactions of alkylidene malonates.: Catalysis by C2-symmetric bis(oxazoline) copper(II) complexes in the synthesis of chiral, differentiated glutarate esters
被引:171
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

Rovis, T
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

Kozlowski, MC
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

Downey, CW
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

Tedrow, JS
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
机构:
[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
关键词:
D O I:
10.1021/ja002246+
中图分类号:
O6 [化学];
学科分类号:
0703 ;
摘要:
Ct-symmetric bis(oxazorine)-Cu(TT) complexes 1 catalyze the Mukaiyama Michael reaction of alkylidene malonates and enolsilanes The use of hexafluoro-2-propanol is essential to induce catalyst turnover. High enantioselectivities are exhibited by bulky alkylidene malonate beta-substituents using catalyst la. The glutarate ester products are readily decarboxylated to provide chiral 1,5-dicarbonyl synthons. Crystallographic characterization of substrate-catalyst complexes provides insight into the binding event with these catalysts and affords a rationale for the observed facial selectivities.
引用
收藏
页码:9134 / 9142
页数:9
相关论文
共 80 条
- [21] Cationic bis(oxazoline) and pyridyl-bis(oxazoline)Cu(II) and Zn(II) Lewis acid catalysts. A comparative study in catalysis of Diels-Alder and aldol reactions[J]. TETRAHEDRON LETTERS, 1996, 37 (42) : 7481 - 7484Evans, DA论文数: 0 引用数: 0 h-index: 0机构: Dept. of Chem. and Chemical Biology, Harvard University, CambridgeKozlowski, MC论文数: 0 引用数: 0 h-index: 0机构: Dept. of Chem. and Chemical Biology, Harvard University, CambridgeTedrow, JS论文数: 0 引用数: 0 h-index: 0机构: Dept. of Chem. and Chemical Biology, Harvard University, Cambridge
- [22] C-2-symmetric copper(II) complexes as chiral Lewis acids. Catalytic enantioselective aldol additions of enolsilanes to pyruvate esters[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (33) : 7893 - 7894Evans, DA论文数: 0 引用数: 0 h-index: 0机构: Dept. Chemistry and Chemical Biology, Harvard University, CambridgeKozlowski, MC论文数: 0 引用数: 0 h-index: 0机构: Dept. Chemistry and Chemical Biology, Harvard University, CambridgeBurgey, CS论文数: 0 引用数: 0 h-index: 0机构: Dept. Chemistry and Chemical Biology, Harvard University, CambridgeMacMillan, DWC论文数: 0 引用数: 0 h-index: 0机构: Dept. Chemistry and Chemical Biology, Harvard University, Cambridge
- [23] C2-symmetric copper(II) complexes as chiral Lewis acids.: Scope and mechanism of the catalytic enantioselective aldol additions of enolsilanes to pyruvate esters[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (04) : 686 - 699Evans, 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 USABurgey, CS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 USAKozlowski, MC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 USATregay, SW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
- [24] Bis(oxazoline) and bis(oxazolinyl)pyridine copper complexes as enantioselective Diels-Alder catalysts: Reaction scope and synthetic applications[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (33) : 7582 - 7594Evans, 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 USABarnes, DM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 USAJohnson, JS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 USALectka, R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 USAvon Matt, P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 USAMiller, SJ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 USAMurry, JA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 USANorcross, RD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 USAShaughnessy, EA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 USACampos, KR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
- [25] Catalytic enantioselective amination of enolsilanes using C2-symmetric copper(II) complexes as chiral Lewis acids[J]. ORGANIC LETTERS, 1999, 1 (04) : 595 - 598Evans, 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 USAJohnson, DS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
- [26] Catalytic enantioselective hetero Diels-Alder reactions of α,β-unsaturated acyl phosphonates with enol ethers[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (19) : 4895 - 4896Evans, 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 USAJohnson, JS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
- [27] C2-symmetric copper(II) complexes as chiral Lewis acids.: Enantioselective catalysis of the glyoxylate-ene reaction[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (23) : 5824 - 5825Evans, 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 USABurgey, CS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 USAParas, NA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 USAVojkovsky, T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 USATregay, SW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
- [28] An improved procedure for the preparation of 2,2-bis[2-[4(S)-tert-butyl-1,3-oxazolinyl]]propane [(S,S)-tert-butylbis(oxazoline)] and derived copper(II) complexes[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (13) : 4541 - 4544Evans, DA论文数: 0 引用数: 0 h-index: 0机构: MIT, Dept Chem & Biol Chem, Cambridge, MA 02139 USA MIT, Dept Chem & Biol Chem, Cambridge, MA 02139 USAPeterson, GS论文数: 0 引用数: 0 h-index: 0机构: MIT, Dept Chem & Biol Chem, Cambridge, MA 02139 USA MIT, Dept Chem & Biol Chem, Cambridge, MA 02139 USAJohnson, JS论文数: 0 引用数: 0 h-index: 0机构: MIT, Dept Chem & Biol Chem, Cambridge, MA 02139 USA MIT, Dept Chem & Biol Chem, Cambridge, MA 02139 USABarnes, DM论文数: 0 引用数: 0 h-index: 0机构: MIT, Dept Chem & Biol Chem, Cambridge, MA 02139 USA MIT, Dept Chem & Biol Chem, Cambridge, MA 02139 USACampos, KR论文数: 0 引用数: 0 h-index: 0机构: MIT, Dept Chem & Biol Chem, Cambridge, MA 02139 USA MIT, Dept Chem & Biol Chem, Cambridge, MA 02139 USAWoerpel, KA论文数: 0 引用数: 0 h-index: 0机构: MIT, Dept Chem & Biol Chem, Cambridge, MA 02139 USA MIT, Dept Chem & Biol Chem, Cambridge, MA 02139 USA
- [29] Reversal in enantioselectivity of tert-butyl versus phenyl-substituted bis(oxazoline)copper(II) catalyzed hetero Diels-Alder and ene reactions.: Crystallographic and mechanistic studies[J]. TETRAHEDRON LETTERS, 1999, 40 (15) : 2879 - 2882Evans, 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 USAJohnson, JS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 USABurgey, CS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 USACampos, KR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
- [30] Cationic bis(oxazoline)Cu(II) Lewis acid catalysts. Enantioselective furan Diels-Alder reaction in the synthesis of ent-shikimic acid[J]. TETRAHEDRON LETTERS, 1997, 38 (01) : 57 - 58Evans, DA论文数: 0 引用数: 0 h-index: 0机构: Department of Chemistry, Harvard University, CambridgeBarnes, DM论文数: 0 引用数: 0 h-index: 0机构: Department of Chemistry, Harvard University, Cambridge