An efficient method for the preparation of chiral Mosher's acid analogues

被引:20
作者
Kawano, Y
Kaneko, N
Mukaiyama, T
机构
[1] Kitasato Univ, Kitasato Inst Life Sci, Minato Ku, Tokyo 1088641, Japan
[2] Kitasato Inst, Ctr Basic Res, Kita Ku, Tokyo 1140003, Japan
关键词
D O I
10.1246/cl.2006.304
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A diastereoselective trifluoromethylation of chiral alpha-keto esters derived from isosorbide with TMSCF3 in the presence of a Lewis-base catalyst gave the corresponding trifluoromethylated alpha-hydroxy esters in good yields with moderate to high diastereomeric excesses.
引用
收藏
页码:304 / 305
页数:2
相关论文
共 21 条
[1]   SELECTIVE ALKYLATIONS OF 1,4/3,6-DIANHYDRO-D-GLUCITOL (ISOSORBIDE) [J].
ABENHAIM, D ;
LOUPY, A ;
MUNNIER, L ;
TAMION, R ;
MARSAIS, F ;
QUEGUINER, G .
CARBOHYDRATE RESEARCH, 1994, 261 (02) :255-266
[2]   A SHORT ROUTE TO A MOSHERS ACID PRECURSOR VIA CATALYTIC ASYMMETRIC DIHYDROXYLATION (AD) [J].
BENNANI, YL ;
VANHESSCHE, KPM ;
SHARPLESS, KB .
TETRAHEDRON-ASYMMETRY, 1994, 5 (08) :1473-1476
[3]   Catalytic aerobic oxidative decarboxylation of α-trifluoromethyl-α-hydroxy acids to trifluoromethyl ketones [J].
Blay, G ;
Fernández, I ;
Marco-Aleixandre, A ;
Monje, B ;
Pedro, JR ;
Ruiz, R .
TETRAHEDRON, 2002, 58 (42) :8565-8571
[4]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[5]   A new entry to asymmetric synthesis of optically active α,γ-substituted γ-butyrolactones, using a carbohydrate derived amide as both a chiral auxiliary and a proton source [J].
Huang, LL ;
Xu, MH ;
Lin, GQ .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02) :529-532
[6]   A MODIFIED SYNTHESIS OF MOSHERS ACID AND ITS USE IN A SENSITIVE STEREOISOMER ANALYSIS OF AMINO-ACID DERIVATIVES [J].
HULL, WE ;
SEEHOLZER, K ;
BAUMEISTER, M ;
UGI, I .
TETRAHEDRON, 1986, 42 (02) :547-552
[7]   Diastereoselective trifluoromethylation of chiral N-(tolylsulfinyl)imines in the presence of Lewis bases [J].
Kawano, Y ;
Mukaiyama, T .
CHEMISTRY LETTERS, 2005, 34 (07) :894-895
[8]   Lewis base-catalyzed trifluoromethylation of aldimines with (trifluoromethyl)trimethylsilane [J].
Kawano, Y ;
Fujisawa, H ;
Mukaiyama, T .
CHEMISTRY LETTERS, 2005, 34 (03) :422-423
[9]   Isomannide and isosorbide as new chiral auxiliaries for the stereoselective synthesis of tertiary α-hydroxy acids [J].
Loupy, A ;
Monteux, DA .
TETRAHEDRON, 2002, 58 (08) :1541-1549
[10]   Asymmetric Diels-Alder: Monobenzylated isosorbide and isomannide as highly effective chiral auxiliaries [J].
Loupy, A ;
Monteux, D .
TETRAHEDRON LETTERS, 1996, 37 (39) :7023-7026