Synthesis of enantiomerically pure α-ethyl, α-vinyl and α-ethynyl 3,3,3-trifluoro alaninates

被引:38
作者
Crucianelli, M
De Angelis, F
Lazzaro, F
Malpezzi, L
Volonterio, A
Zanda, M
机构
[1] CNR, Ist Chim Riconoscimento Mol, Sez A Quilico, I-20131 Milan, Italy
[2] Univ Aquila, Dipartimento Chim Ingn Chim & Mat, I-67010 Coppito, Italy
[3] Politecn Milan, Dipartimento Chim Mat & Ingn Chim G Natta, I-20131 Milan, Italy
关键词
trifluoromethyl; alpha-amino acids; sulfinimine; stereoselective;
D O I
10.1016/j.jfluchem.2003.11.034
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
We describe the first synthesis of enantiomerically pure (S)-alpha-vinyl and (S)-alpha-ethynyl 3,3,3-trifluoro alanine (TF-Ala) ethyl esters, starting from the in situ generated sulfinimine (S)-2 as key fluorinated building-block. (S)-alpha-Ethyl TF-Ala-OEt has been prepared as well by this route. (C) 2004 Elsevier B.V. All rights reserved.
引用
收藏
页码:573 / 577
页数:5
相关论文
共 13 条
[1]   SIR97:: a new tool for crystal structure determination and refinement [J].
Altomare, A ;
Burla, MC ;
Camalli, M ;
Cascarano, GL ;
Giacovazzo, C ;
Guagliardi, A ;
Moliterni, AGG ;
Polidori, G ;
Spagna, R .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1999, 32 :115-119
[2]  
Asensio A, 2001, EUR J ORG CHEM, V2001, P1449
[3]  
BAKS RE, 1994, ORGANOFLUORINE CHEM
[4]   Sulfinimines of trifluoropyruvate:: Novel intermediates for chiral non racemic α-trifluoromethyl α-amino acids [J].
Bravo, P ;
Crucianelli, M ;
Vergani, B ;
Zanda, M .
TETRAHEDRON LETTERS, 1998, 39 (42) :7771-7774
[5]  
BURGER K, 1990, SYNTHESIS-STUTTGART, P115
[6]  
BURGER K, 1992, LIEBIGS ANN CHEM, P947
[7]   ON ENANTIOMORPH-POLARITY ESTIMATION [J].
FLACK, HD .
ACTA CRYSTALLOGRAPHICA SECTION A, 1983, 39 (NOV) :876-881
[8]   Φ-Values beyond the ribosomally encoded amino acids:: Kinetic and thermodynamic consequences of incorporating trifluoromethyl amino acids in a globular protein [J].
Horng, JC ;
Raleigh, DP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (31) :9286-9287
[9]  
Kukhar VP., 1995, FLUORINE CONTAINING
[10]   New efficient syntheses of alpha-difluoromethyl- and alpha-trifluoromethyl-ornithine [J].
Osipov, SN ;
Golubev, AS ;
Sewald, N ;
Burger, K .
TETRAHEDRON LETTERS, 1997, 38 (34) :5965-5966