Effect of additives on the proline-catalyzed ketone-aldehyde aldol reactions

被引：222

作者：

Pihko, PM ^{[1
]}

Laurikainen, KM ^{[1
]}

Usano, A ^{[1
]}

Nyberg, AI ^{[1
]}

Kaavi, JA ^{[1
]}

机构：

[1] Aalto Univ, Dept Chem Technol, FI-02015 Helsinki, Finland

来源：

TETRAHEDRON | 2006年 / 62卷 / 2-3期

基金：

芬兰科学院;

关键词：

aldehydes; aldol reactions; bases; ketones; organocatalysis; proline; water;

D O I：

10.1016/j.tet.2005.09.070

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The effect of bases, acids, and water as additives in profine-catalyzed ketone-aldehyde aldol reactions has been studied. While the reaction appears to be relatively tolerant to small amounts of tertiary amine bases or weak acids, it stops completely with strong acids. The use of water as an additive had a highly beneficial effect on reactions that were conducted with a stoichiometric ratio of ketone to aldehyde, especially with cyclic ketones. This allows the efficient use of more precious ketones such as 4-thianone as donors in the direct enantioselective aldol and facilitates purification. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：317 / 328

页数：12

共 50 条

[1] Proline-catalyzed ketone-aldehyde aldol reactions are accelerated by water
Nyberg, AI
Usano, A
Pihko, PM
[J]. SYNLETT, 2004, (11) : 1891 - 1896
[2] Switching Diastereoselectivity in Proline-Catalyzed Aldol Reactions
Martinez-Castaneda, Angel
Rodriguez-Solla, Humberto
Concellon, Carmen
del Amo, Vicente
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22): : 10375 - 10381
[3] Proline-catalyzed direct asymmetric aldol reactions
[J]. 1600, ACS, Washington, DC, USA (122):
[4] Proline-catalyzed direct asymmetric aldol reactions
List, B
Lerner, RA
Barbas, CF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (10) : 2395 - 2396
[5] 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
[6] Transition states for proline-catalyzed asymmetric aldol reactions.
Bahmanyar, S
Houk, KN
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 221 : U98 - U98
[7] Proline-catalyzed tandem aldol and alkylation reactions in alcoholic medium
Zhao, CG
Rajasekhar, D
Liu, JY
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3075 - U3076
[8] Origins of the double asymmetric induction on proline-catalyzed aldol reactions
Calderon, Felix
Doyagueez, Elisa G.
Cheong, Paul Ha-Yeon
Fernandez-Mayoralas, Alfonso
Houk, K. N.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (20): : 7916 - 7920
[9] Tetrahydrobenzo[5]helicenediol derivatives as additives for efficient proline-catalyzed asymmetric List-Lerner-Barbas aldol reactions of bulky aldehyde substrates
Fang, Lei
lin, Weibin
Chen, Chuanfeng
[J]. CHINESE CHEMICAL LETTERS, 2018, 29 (08) : 1223 - 1225
[10] Tetrahydrobenzo[5]helicenediol derivatives as additives for efficient proline-catalyzed asymmetric List-Lerner-Barbas aldol reactions of bulky aldehyde substrates
Lei Fang
Weibin Lin
Chuanfeng Chen
[J]. Chinese Chemical Letters, 2018, 29 (08) : 1223 - 1225

← 1 2 3 4 5 →