4-Substituted prolyl sulfonamides as enantioselective organocatalysts for aldol reactions

被引：54

作者：

Bellis, E ^{[1
]}

Vasilatou, K ^{[1
]}

Kokotos, G ^{[1
]}

机构：

[1] Univ Athens, Dept Chem, Organ Chem Lab, Athens 15771, Greece

来源：

SYNTHESIS-STUTTGART | 2005年 / 14期

关键词：

aldol reactions; amino acids; asymmetric catalysis; catalysis; sulfonamides;

D O I：

10.1055/s-2005-870026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of prolyl and 4-substituted prolyl sulfonamides were prepared and were evaluated as organocatalysts of asymmetric aldol reaction. Using prolyl methanesulfonamide, 4-benzyloxy-prolyl methanesulfonamide and toluenesulfonamide and 4-hydroxyprolyl toluenesulfonamide the aldol product was obtained in much higher enantiomeric excess (ee) in comparison to that observed using proline itself. In addition, these new catalysts may be used in lower sub-stoichiometric amounts than proline, because of their improved solubility in organic solvents.

引用

页码：2407 / 2413

页数：7

共 38 条

[1] Studies on the transformation of azido-group to N-(t-butoxycarbonyl)amino group via Staudinger reaction
Afonso, CAM
[J]. SYNTHETIC COMMUNICATIONS, 1998, 28 (02) : 261 - 276
[2] Theory of asymmetric organocatalysis of aldol and related reactions: Rationalizations and predictions
Allemann, C
Gordillo, R
Clemente, FR
Cheong, PHY
Houk, KN
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) : 558 - 569
[3] The origin of stereoselectivity in proline-catalyzed intramolecular aldol reactions
Bahmanyar, S
Houk, KN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (51) : 12911 - 12912
[4] Proline-derived N-sullfonylcarboxamides:: Readily available, highly enantioselective and versatile catalysts for direct aldol reactions
Berkessel, A
Koch, B
Lex, J
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) : 1141 - 1146
[5] Catalytic enantioselective direct Michael additions of ketones to alkylidene malonates
Betancort, JM
Sakthivel, K
Thayumanavan, R
Barbas, CF
[J]. TETRAHEDRON LETTERS, 2001, 42 (27) : 4441 - 4444
[6] The direct and enantioselective organocatalytic α-oxidation of aldehydes
Brown, SP
Brochu, MP
Sinz, CJ
MacMillan, DWC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) : 10808 - 10809
[7] Organocatalysis with proline derivatives: improved catalysts for the asymmetric Mannich, nitro-Michael and aldol reactions
Cobb, AJA
Shaw, DM
Longbottom, DA
Gold, JB
Ley, SV
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (01) : 84 - 96
[8] 5-pyrrolidin-2-yltetrazole: A new, catalytic, more soluble alternative to proline in an organocatalytic asymmetric Mannich-type reaction
Cobb, AJA
Shaw, DM
Ley, SV
[J]. SYNLETT, 2004, (03) : 558 - 560
[9] The direct catalytic asymmetric cross-Mannich reaction:: A highly enantioselective route to 3-amino alcohols and α-amino acid derivatives
Córdova, A
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (08) : 1987 - 1997
[10] The direct catalytic asymmetric Mannich reaction
Córdova, A
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (02) : 102 - 112

← 1 2 3 4 →