Enantioselective addition of oxazolones to N-protected imines catalysed by chiral thioureas

被引：15

作者：

Zabka, Matej ^{[1
]}

Malastova, Andrea ^{[1
]}

Sebesta, Radovan ^{[1
]}

机构：

[1] Comenius Univ, Dept Organ Chem, Fac Nat Sci, SK-84215 Bratislava, Slovakia

来源：

RSC ADVANCES | 2015年 / 5卷 / 17期

关键词：

ALPHA-AMINO-ACIDS; ALPHA; BETA-DIAMINO ACIDS; MICHAEL ADDITION; ORGANOCATALYTIC ADDITION; ASYMMETRIC CATALYSIS; MANNICH REACTIONS; AZLACTONES; DERIVATIVES; SQUARAMIDES; UREA;

D O I：

10.1039/c5ra00092k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Hydrogen bond-catalysed aza-Mannich addition of oxazolones to various protected aldimines has been developed. The resulting, highly functionalized, oxazolones contain a quaternary stereogenic centre and can serve as precursors for chiral alpha,beta-diamino acids with different protecting groups on each amino group. The process benefits from the versatile bifunctional thiourea catalysts, which effect the formation of these products in high yields and stereoselectivities.

引用

页码：12890 / 12893

页数：4

共 50 条

[41] Chiral Squaramide-Catalyzed Enantioselective Decarboxylative Addition of -Keto Acids to Isatin Imines
Kaur, Jasneet
Kumari, Anita
Bhardwaj, Vimal K.
Chimni, Swapandeep Singh
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (10) : 1725 - 1734
[42] The first use of chiral oxazoline ligands in the highly enantioselective diethylzinc addition to diphenylphosphinoyl imines
Zhang, XM
Lin, WQ
Gong, LZ
Mi, AQ
Cui, X
Jiang, YZ
Choi, MCK
Chan, ASC
TETRAHEDRON LETTERS, 2002, 43 (08) : 1535 - 1537
[43] Enantioselective addition of hydrogen cyanide to imines catalyzed by a chiral (salen)Al(III) complex
Sigman, MS
Jacobsen, EN
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (21) : 5315 - 5316
[44] Chiral Phosphoric Acid Catalyzed Enantioselective Friedel-Crafts Reaction of N-Protected 4-Aminoindoles with β,γ-Unsaturated α-Ketimino Esters
Ding, Yu-Yang
Xu, Deng-Feng
Meng, Shan-Shui
Li, Yang
Zhao, Jun-Ling
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (04) : 664 - 669
[45] Chiral imidazole derivatives synthesis from enantiopure N-protected α-amino acids
Bures, F
Kulhánek, J
TETRAHEDRON-ASYMMETRY, 2005, 16 (07) : 1347 - 1354
[46] N-Heterocyclic carbene catalysed umpolung reactions of imines approaching enantioselective synthesis
Chauhan, Pankaj
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (23): : 3821 - 3824
[47] SYNTHESIS OF CHIRAL N-PROTECTED BETA-AMINO ALCOHOLS BY THE USE OF UNCAS
FEHRENTZ, JA
CALIFANO, JC
AMBLARD, M
MARTINEZ, J
LOFFET, A
TETRAHEDRON LETTERS, 1994, 35 (04) : 569 - 571
[48] Generation and asymmetric Michael addition reaction of chirally N-protected α-aminoalkyl cyanocuprates
Tomoyasu, T
Tomooka, K
Nakai, T
TETRAHEDRON LETTERS, 2000, 41 (03) : 345 - 349
[49] Enantioselective copper catalysed 1,4-conjugate addition reactions using chiral N-heterocyclic carbenes
Winn, CL
Guillen, F
Pytkowicz, J
Roland, S
Mangeney, P
Alexakis, A
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (24-25) : 5672 - 5695
[50] Protease-catalysed coupling of N-protected amino acids and peptides with 4-aminoantipyrine
Lang, Alexander
Hatscher, Catharina
Wiegert, Charline
Kuhl, Peter
AMINO ACIDS, 2009, 36 (02) : 333 - 340

← 1 2 3 4 5 →