Enantioselective Syn-selective scandium-catalyzed ene reactions

被引：88

作者：

Evans, DA ^{[1
]}

Wu, J ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 22期

关键词：

D O I：

10.1021/ja0522130

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An enantio- and diastereoselective carbonyl-ene reaction catalyzed by chiral scandium pyridyl bis(oxazoline) (pybox) complexes has been developed. Uniformly high enantiomeric excesses and good yields were observed. Use of trisubstituted olefins generated the syn product in high enantio- and diastereoselectivity. Copyright © 2005 American Chemical Society.

引用

页码：8006 / 8007

页数：2

共 29 条

[1] Asymmetric catalysis of ene reactions with trifluoropyruvate catalyzed by dicationic palladium(II) complexes
Aikawa, K
Kainuma, S
Hatano, M
Mikami, K
[J]. TETRAHEDRON LETTERS, 2004, 45 (01) : 183 - 185
[2] CATALYTIC ASYMMETRIC CARBONYL-ENE REACTIONS
BERRISFORD, DJ
BOLM, C
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (16): : 1717 - 1719
[3] CATALYTIC, ENANTIOSELECTIVE ACETONE ALDOL ADDITIONS WITH 2-METHOXYPROPENE
CARREIRA, EM
LEE, W
SINGER, RA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (12) : 3649 - 3650
[4] Concise synthesis of conformationally constrained pybox ligands
Davies, IW
Gerena, L
Lu, N
Larsen, RD
Reider, PJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) : 9629 - 9630
[5] A general method for the enantioselective synthesis of pantolactone derivatives
Evans, DA
Wu, J
Masse, CE
MacMillan, DWC
[J]. ORGANIC LETTERS, 2002, 4 (20) : 3379 - 3382
[6] C2-symmetric Sc(III)-complexes chiral Lewis acids.: Catalytic enantioselective aldol additions glyoxylate esters
Evans, DA
Masse, CE
Wu, J
[J]. ORGANIC LETTERS, 2002, 4 (20) : 3375 - 3378
[7] Highly enantioselective syntheses of homopropargylic alcohols and dihydrofurans catalyzed by a bis(oxazolinyl)pyridine-scandium triflate complex
Evans, DA
Sweeney, ZK
Rovis, T
Tedrow, JS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (48) : 12095 - 12096
[8] C2-symmetric copper(II) complexes as chiral Lewis acids.: Catalytic enantioselective carbonyl-ene reactions with glyoxylate and pyruvate esters
Evans, DA
Tregay, SW
Burgey, CS
Paras, NA
Vojkovsky, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (33) : 7936 - 7943
[9] Mild nitrosation and hydrolysis of polyfunctional amides
Evans, DA
Carter, PH
Dinsmore, CJ
Barrow, JC
Katz, JL
Kung, DW
[J]. TETRAHEDRON LETTERS, 1997, 38 (26) : 4535 - 4538
[10] Enantioselective indole Friedel-Crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes
Evans, DA
Scheidt, KA
Fandrick, KR
Lam, HW
Wu, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) : 10780 - 10781

← 1 2 3 →