Sidearm effect: Improvement of the enantiomeric excess in the asymmetric Michael addition of indoles to alkylidene malonates

被引：262

作者：

Zhou, J ^{[1
]}

Tang, Y ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 31期

关键词：

D O I：

10.1021/ja026936k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A pseudo-C3-trisoxazoline was designed and synthesized. The improvement of the traditional bisoxazoline into a novel trisoxazoline by a sidearm approach resulted in highly catalytic enantioselective Michael addition of indoles to alkylidene malonates. Excellent catalytic reactivity and enantioselectivity (up to 99% yield and 93% ee) were achieved. Copyright © 2002 American Chemical Society.

引用

页码：9030 / 9031

页数：2

共 39 条

[1] Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis
Austin, JF
MacMillan, DWC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) : 1172 - 1173
[2] From indomethacin to a selective COX-2 inhibitor: Development of indolalkanoic acids as potent and selective cyclooxygenase-2 inhibitors
Black, WC
Bayly, C
Belley, M
Chan, CC
Charleson, S
Denis, D
Gauthier, JY
Gordon, R
Guay, D
Kargman, S
Lau, CK
Leblanc, Y
Mancini, J
Ouellet, M
Percival, D
Roy, P
Skorey, K
Tagari, P
Vickers, P
Wong, E
Xu, L
Prasit, P
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (06) : 725 - 730
[3] Catalytic asymmetric Henry reactions -: a simple approach to optically active β-nitro α-hydroxy esters
Christensen, C
Juhl, K
Jorgensen, KA
[J]. CHEMICAL COMMUNICATIONS, 2001, (21) : 2222 - 2223
[4] Preparation and catalytic enantioselective reactions of C3-symmetric tris(oxazoline)s derived from Kemp's triacid
Chuang, TH
Fang, JM
Bolm, C
[J]. SYNTHETIC COMMUNICATIONS, 2000, 30 (09) : 1627 - 1641
[5] Chiral bis(oxazoline)copper(II) complexes as Lewis acid catalysts for the enantioselective Diels-Alder reaction
Evans, DA
Miller, SJ
Lectka, T
von Matt, P
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (33) : 7559 - 7573
[6] C2-symmetric Cu(II) complexes as chiral Lewis acids.: Catalytic, enantioselective cycloadditions of silyl ketenes
Evans, DA
Janey, JM
[J]. ORGANIC LETTERS, 2001, 3 (13) : 2125 - 2128
[7] Chiral copper(II) complexes as Lewis acids for catalyzed cycloaddition, carbonyl addition, and conjugate addition reactions
Evans, DA
Rovis, T
Johnson, JS
[J]. PURE AND APPLIED CHEMISTRY, 1999, 71 (08) : 1407 - 1415
[8] Catalytic enantioselective Michael additions to unsaturated ester derivatives using chiral copper(II) Lewis acid complexes
Evans, DA
Willis, MC
Johnston, JN
[J]. ORGANIC LETTERS, 1999, 1 (06) : 865 - 868
[9] C2-symmetric Cu(II) complexes as chiral Lewis acids.: Catalytic enantioselective Michael addition of silylketene acetals to alkylidene malonates
Evans, DA
Rovis, T
Kozlowski, MC
Tedrow, JS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (09) : 1994 - 1995
[10] C-2-symmetric copper(II) complexes as chiral Lewis acids. Catalytic enantioselective aldol additions of silylketene acetals to (benzyloxy)acetaldehyde
Evans, DA
Murry, JA
Kozlowski, MC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (24) : 5814 - 5815

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