Straightforward synthesis of enantiopure (R)- and (S)-trifluoroalaninol

被引:10
|
作者
Pytkowicz, Julien [1 ]
Stephany, Olivier [1 ]
Marinkovic, Sinisa [1 ]
Inagaki, Sebastien [1 ]
Brigaud, Thierry [1 ]
机构
[1] Univ Cergy Pontoise, Lab SOSCO, F-95000 Cergy Pontoise, France
关键词
BETA-AMINO ALCOHOLS; ASYMMETRIC-SYNTHESIS; ALPHA-AMINO; STEREOSELECTIVE-SYNTHESIS; ETHYL TRIFLUOROPYRUVATE; CHIRAL AUXILIARIES; 1,2-AMINO ALCOHOLS; EFFICIENT APPROACH; CONTAINING LIGANDS; BUILDING-BLOCKS;
D O I
10.1039/c0ob00424c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two efficient routes are reported for the synthesis of both enantiomers of trifluoroalaninol in enantiopure form. The first pathway involves a Strecker-type reaction performed from a chiral trifluoromethyloxazolidine (Fox). The second route, which is more direct, involves, as a key step, the reduction of chiral oxazolidines or imines derived from ethyl trifluoropyruvate.
引用
收藏
页码:4540 / 4542
页数:3
相关论文
共 50 条
  • [21] Straightforward synthesis of enantiopure 2-aminomethyl and 2-hydroxymethyl pyrrolidines with complete stereocontrol
    Marradi, M
    Cicchi, S
    Delso, JI
    Rosi, L
    Tejero, T
    Merino, P
    Goti, A
    TETRAHEDRON LETTERS, 2005, 46 (08) : 1287 - 1290
  • [22] Convenient synthesis of enantiopure (R-) and (S-)-3-fluoro-3-aminomethylpyrrolidines
    Yarmolchuk, Vladimir S.
    Mykhalchuk, Vladimir L.
    Mykhailiuk, Pavel K.
    TETRAHEDRON, 2014, 70 (18) : 3011 - 3017
  • [23] Synthesis of enantiopure cyclopentitols and aminocyclopentitols mediated by oxyselenenylation of cyclopentene with (R,R)-hydrobenzoin
    Kim, KS
    Park, JI
    Ding, PY
    TETRAHEDRON LETTERS, 1998, 39 (36) : 6471 - 6474
  • [24] An Efficient Synthesis of Enantiopure (2R,3R)-β-Methoxytyrosine
    Fan, Shi-Ming
    Tian, Xia
    Yang, Yi-Hua
    Jin, Long Yi
    Liu, Shou-xin
    SYNLETT, 2015, 26 (18) : 2553 - 2556
  • [25] Straightforward synthesis of enantiopure tfm-amino acids from chiral CF3-oxazolidines
    Brigaud, Thierry
    Chaume, Gregory
    Huguenot, Florent
    Caupene, Caroline
    JOURNAL OF PEPTIDE SCIENCE, 2008, 14 (08) : 54 - 54
  • [26] Straightforward Synthesis of Enantiopure 2,3-Dihydrobenzofurans by a Sequential Stereoselective Biotransformation and Chemical Intramolecular Cyclization
    Mangas-Sanchez, Juan
    Busto, Eduardo
    Gotor-Fernandez, Vicente
    Gotor, Vicente
    ORGANIC LETTERS, 2010, 12 (15) : 3498 - 3501
  • [27] Synthesis of enantiopure (S)-thieno[f]indolizidines
    Marchalin, S
    Szemes, F
    Bar, N
    Decroix, B
    HETEROCYCLES, 1999, 50 (01) : 445 - 452
  • [28] Convenient synthesis of enantiopure β-adrenergic blockers:: (R)-nifenalol, (R)-denopamine, (R)-dichloroisoproterenol and (R)-pronethalol
    Cho, BT
    Kang, SK
    Yang, WK
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2002, 23 (09) : 1328 - 1330
  • [29] An integrated chemoenzymatic synthesis of enantiopure (-)-(1R,5S)-cyclosarkomycin: A sarkomycin precursor
    Andrau, L
    Lebreton, J
    Viazzo, P
    Alphand, V
    Furstoss, R
    TETRAHEDRON LETTERS, 1997, 38 (05) : 825 - 826
  • [30] A Straightforward Synthesis of Enantiopure 2,6-Disubstituted Morpholines by a Regioselective O-Protection/Activation Protocol
    Penso, Michele
    Lupi, Vittoria
    Albanese, Domenico
    Foschi, Francesca
    Landini, Dario
    Tagliabue, Aaron
    SYNLETT, 2008, (16) : 2451 - 2454