Peptide-catalyzed 1,4-Addition Reactions of Aldehydes to Nitroolefins

被引：3

作者：

Kastl, Robert ^{[1
]}

Arakawa, Yukihiro ^{[1
]}

Duschmale, Joerg ^{[1
]}

Wiesner, Markus ^{[1
]}

Wennemers, Helma ^{[1
]}

机构：

[1] Swiss Fed Inst Technol, Organ Chem Lab, CH-8093 Zurich, Switzerland

来源：

CHIMIA | 2013年 / 67卷 / 04期

关键词：

Asymmetric catalysis; Conjugate addition reaction; Nitroolefins; Organocatalysis; Peptides; CONJUGATE ADDITION-REACTIONS; ASYMMETRIC MICHAEL ADDITION; X-RAY-CRYSTAL; SUBSTRATE COIMMOBILIZATION; EFFICIENT ORGANOCATALYSTS; ENAMINE CATALYSIS; NMR-SOLUTION; KETONES; GAMMA; BETA;

D O I：

10.2533/chimia.2013.279

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Conjugate addition reactions of aldehydes to nitroolefins provide synthetically useful gamma-nitroaldehydes. Here we summarize our research on peptide-catalyzed conjugate addition reactions of aldehydes to differently substituted nitroolefins. We show that peptides of the general type Pro-Pro-Xaa (Xaa = acidic amino acid) are not only highly active, robust and stereoselective catalysts but have also remarkable chemoselectivities.

引用

下载

页码：279 / 282

页数：4

共 50 条

[31] UTILIZATION OF MIXED METHYLMAGNESIOCUPRATES IN 1,4-ADDITION REACTIONS
LEYENDECKER, F
DROUIN, J
DEBESSE, JJ
CONIA, JM
TETRAHEDRON LETTERS, 1977, (18) : 1591 - 1594
[32] 1,4-ADDITION OF LITHIUM AND MAGNESIUM DERIVATIVES OF ORTHO CARBORANES TO ALPHA, BETA NITROOLEFINS
KAZANTSEV, AV
AKSARTOV, MM
ZAKHARKI.LI
ZHURNAL OBSHCHEI KHIMII, 1971, 41 (03): : 711 - +
[33] Chiral α-Amino Phosphonates via Rhodium-Catalyzed Asymmetric 1,4-Addition Reactions
Lefevre, Nicolas
Brayer, Jean-Louis
Folleas, Benoit
Darses, Sylvain
ORGANIC LETTERS, 2013, 15 (16) : 4274 - 4276
[34] Enantioselective 1,4-addition reactions of diphenyl phosphite to nitroalkenes catalyzed by an axially chiral guanidine
Terada, Masahiro
Ikehara, Takashi
Ube, Hitoshi
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (46) : 14112 - +
[35] Rhodium-catalyzed 1,4-addition reactions of diboron reagents to electron deficient olefins
Kabalka, GW
Das, BC
Das, S
TETRAHEDRON LETTERS, 2002, 43 (13) : 2323 - 2325
[36] STEREOCONTROLLED LACTONIZATION REACTIONS VIA PALLADIUM-CATALYZED 1,4-ADDITION TO CONJUGATED DIENES
BACKVALL, JE
GRANBERG, KL
ANDERSSON, PG
GATTI, R
GOGOLL, A
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20): : 5445 - 5451
[37] Heteroarylboronates in Rhodium-Catalyzed 1,4-Addition to Enones
Albrecht, Fabian
Sowada, Oliver
Fistikci, Meryem
Boysen, Mike M. K.
ORGANIC LETTERS, 2014, 16 (19) : 5212 - 5215
[38] Iron-Catalyzed 1,4-Addition of α-Olefins to Dienes
Moreau, Benoit
Wu, Jessica Y.
Ritter, Tobias
ORGANIC LETTERS, 2009, 11 (02) : 337 - 339
[39] 1,4-Addition of silicon dienoates to α,β-unsaturated aldehydes catalyzed by in situ-generated silicon Lewis acid
Yanai, Hikaru
Takahashi, Arata
Taguchi, Takeo
CHEMICAL COMMUNICATIONS, 2010, 46 (46) : 8728 - 8730
[40] Asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated aldehydes catalyzed by a chiral diene-rhodium complex
Hayashi, T
Tokunaga, N
Okamoto, K
Shintani, R
CHEMISTRY LETTERS, 2005, 34 (11) : 1480 - 1481

← 1 2 3 4 5 →