Lewis base activation of Lewis acids: Vinylogous aldol additions of silyl dienol ethers to aldehydes

被引：32

作者：

Denmark, SE ^{[1
]}

Heemstra, JR ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA

来源：

SYNLETT | 2004年 / 13期

关键词：

Lewis base; asymmetric catalysis; vinylogous aldol reactions; ketones; regioselectivity;

D O I：

10.1055/s-2004-834789

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly regioselective vinylogous aldol additions of silyl dienol ethers derived from simple alpha,beta-unsaturated ketones are described. The catalyst system of silicon tetrachloride activated by chiral bisphosphoramide (R,R)-1 effectively promotes the addition of both gamma-substituted and unsubstituted silyl dienol ethers to a variety of aldehydes with exclusive gamma-regioselectivity and good to excellent diastereo- and enantioselectivity.

引用

页码：2411 / 2416

页数：6

共 50 条

[1] Lewis base activation of Lewis acids: Vinylogous aldol additions of sillyl dienol ethers to alldehydes
Denmark, SE
Heemstra, JR
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3355 - U3356
[2] Lewis base activation of Lewis acids. Vinylogous aldol reactions
[J]. 1600, American Chemical Society (125):
[3] Lewis base activation of Lewis acids.: Vinylogous aldol addition reactions of conjugated N,O-silyl ketene acetals to aldehydes
Denmark, SE
Heemstra, JR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (04) : 1038 - 1039
[4] Lewis base activation of Lewis acids. Vinylogous aldol addition reactions of conjugated N,O-silyl ketene acetals to aldehydes
Denmark, Scott E.
Heemstra, Jr., John R.
[J]. Journal of the American Chemical Society, 2006, 128 (04): : 1038 - 1039
[5] Lewis base activation of lewis acids: Catalytic, enantioselective vinylogous aldol addition reactions
Denmark, Scott E.
Heemstra, John R., Jr.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (15): : 5668 - 5688
[6] Lewis base catalyzed aldol additions of chiral trichlorosilyl enolates and silyl enol ethers
Denmark, SE
Fujimori, S
Pham, SM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (26): : 10823 - 10840
[7] Lewis base activation of Lewis acids. Addition of silyl ketene acetals to aldehydes
Denmark, SE
Wynn, T
Beutner, GL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (45) : 13405 - 13407
[8] Lewis base activation of Lewis acids. Catalytic enantioselective addition of silyl enol ethers of achiral methyl ketones to aldehydes
Denmark, SE
Heemstra, JR
[J]. ORGANIC LETTERS, 2003, 5 (13) : 2303 - 2306
[9] Lewis base activation of Lewis acids: Catalytic, enantioselective addition of silyl ketene acetals to aldehydes
Denmark, SE
Beutner, GL
Wynn, T
Eastgate, MD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) : 3774 - 3789
[10] Lewis base activation of Lewis acids: Catalytic, enantioselective addition of silyl ketene acetals to aldehydes
[J]. Denmark, S.E. (denmark@scs.uiuc.edu), 1600, American Chemical Society (127):

← 1 2 3 4 5 →