Alkynyliodonium Salt Mediated Alkynylation of Azlactones: Fast Access to Cα-Tetrasubstituted α-Amino Acid Derivatives

被引：47
作者：
Finkbeiner, Peter [1 ]
Weckenmann, Nicole M. [1 ]
Nachtsheim, Boris J. [1 ]
机构：
[1] Univ Tubingen, Inst Organ Chem, D-72076 Tubingen, Germany
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 05期
关键词：
CATALYTIC ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ENANTIOSELECTIVE ADDITION; MICHAEL-ADDITION; RECENT PROGRESS; IN-SITU; DIASTEREO; OXAZOL-5-(4H)-ONES; QUATERNIZATION; OXAZOLONES;
D O I：
10.1021/ol500053c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient electrophilic alkynylation of azlactones (oxazol-5(4H)-ones) is developed using alkynyl(phenyl)iodonium salts as the electrophilic alkyne source. After remarkably short reaction times, the desired alkyne functionalized azlactones are obtained in 60-97% yield and can be transformed easily into a variety of quaternary alpha-amino acid derivatives.
引用
收藏
页码：1326 / 1329
页数：4
相关论文
共 60 条
[1]   Enantioselective addition of oxazolones to maleimides. An easy entry to quaternary aminoacids [J].
Alba, Andrea-Nekane R. ;
Valero, Guillem ;
Calbet, Teresa ;
Font-Bardia, Merce ;
Moyano, Albert ;
Rios, Ramon .
NEW JOURNAL OF CHEMISTRY, 2012, 36 (03) :613-618
[2]   Oxazolones in Organocatalysis, New Tricks for an Old Reagent [J].
Alba, Andrea-Nekane R. ;
Rios, Ramon .
CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (03) :720-734
[3]   Enantioselective Organocatalytic Addition of Oxazolones to 1,1-Bis(phenylsulfonyl)ethylene: A Convenient Asymmetric Synthesis of Quaternary α-Amino Acids [J].
Alba, Andrea-Nekane R. ;
Companyo, Xavier ;
Valero, Guillem ;
Moyano, Albert ;
Rios, Ramon .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (18) :5354-5361
[4]   Bronsted Acid Catalyzed Highly Diastereoselective Michael-Type Addition of Azlactones to Enones [J].
Avila, Eloah P. ;
de Mello, Amanda C. ;
Diniz, Renata ;
Amarante, Giovanni W. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (10) :1881-1883
[5]   SYNTHESIS OF ALKYNYL(PHENYL)IODONIUM TRIFLATES AND THEIR REACTION WITH DIETHYL 2-AMINOMALONATE [J].
BACHI, MD ;
BARNER, N ;
CRITTELL, CM ;
STANG, PJ ;
WILLIAMSON, BL .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :3912-3915
[6]   α-vinylic amino acids:: occurrence, asymmetric synthesis, and biochemical mechanisms [J].
Berkowitz, David B. ;
Charette, Bradley D. ;
Karukurichi, Kannan R. ;
McFadden, Jill M. .
TETRAHEDRON-ASYMMETRY, 2006, 17 (06) :869-882
[7]   Synthesis of quaternary amino acids bearing a (2′Z)-fluorovinyl α-branch:: Potential PLP enzyme inactivators [J].
Berkowitz, DB ;
de la Salud-Bea, R ;
Jahng, WJ .
ORGANIC LETTERS, 2004, 6 (11) :1821-1824
[8]   General One-Pot Synthesis of Alkynyliodonium Salts and Alkynyl Benziodoxolones from Aryl Iodides [J].
Bouma, Marinus J. ;
Olofsson, Berit .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (45) :14242-14245
[9]   Electrophilic alkynylation: the dark side of acetylene chemistry [J].
Brand, Jonathan P. ;
Waser, Jerome .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (11) :4165-4179
[10]  
BRAND JP, 2011, J CHEM SOC CHEM COMM, V47, P102, DOI DOI 10.1039/C0CC02265A
123456