A new chiral oxathiane:: synthesis, resolution and absolute configuration determination by vibrational circular dichroism

被引:20
作者
Solladié-Cavallo, A
Balaz, M
Salisova, M
Suteu, C
Nafie, LA
Cao, X
Freedman, TB
机构
[1] Syracuse Univ, Dept Chem, Syracuse, NY 13244 USA
[2] Univ Strasbourg, Lab Stereochim Organomet, CNRS, ECPM, F-67087 Strasbourg, France
[3] Comenius Univ, Dept Organ Chem, Bratislava, Slovakia
[4] Chiral Technol Europe, F-67404 Illkirch Graffenstaden, France
关键词
D O I
10.1016/S0957-4166(01)00441-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A new oxathiane, derived from 5-hydroxy-1-tetralone has been synthesized in eight steps, fully characterized as cis-fused rings by 1D and 2D NMR and resolved by preparative chiral chromatography (CHIRALCEL OD-R). The second eluting (+, MeOH)-isomer was assigned (S,S)-configuration by VCD-ab initio simulation. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2605 / 2611
页数:7
相关论文
共 28 条
[21]  
2-9
[22]   A two-step asymmetric synthesis of pure trans-(R,R)-diaryl-epoxides [J].
SolladieCavallo, A ;
DiepVohuule, A ;
Sunjic, V ;
Vinkovic, V .
TETRAHEDRON-ASYMMETRY, 1996, 7 (06) :1783-1788
[23]   CHIRAL SULFUR-REAGENTS FOR THE PREPARATION OF OPTICALLY-ACTIVE EPOXIDES [J].
SOLLADIECAVALLO, A ;
ADIB, A .
TETRAHEDRON, 1992, 48 (12) :2453-2464
[24]   A 2-STEP ASYMMETRIC-SYNTHESIS OF (R)-MONOARYL EPOXIDES USING A CHIRAL OXATHIANE AS A RECOVERABLE REAGENT - APPLICATION TO THE PREPARATION OF (R)-BETA-ADRENERGIC COMPOUNDS [J].
SOLLADIECAVALLO, A ;
DIEPVOHUULE, A .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (11) :3494-3498
[25]   Determination of absolute configuration using vibrational circular dichroism spectroscopy: The chiral sulfoxide 1-(2-methylnaphthyl) methyl sulfoxide [J].
Stephens, PJ ;
Aamouche, A ;
Devlin, FJ ;
Superchi, S ;
Donnoli, MI ;
Rosini, C .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (11) :3671-3677
[26]   A strategic alternative to solid phase synthesis: Preparation of a small isoxazoline library by ''fluorous synthesis'' [J].
Studer, A ;
Curran, DP .
TETRAHEDRON, 1997, 53 (19) :6681-6696
[27]   Fluorous synthesis: Fluorous protocols for the Ugi and Biginelli multicomponent condensations [J].
Studer, A ;
Jeger, P ;
Wipf, P ;
Curran, DP .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (09) :2917-2924
[28]  
STUDER A, 1997, TETRAHEDRON, P1997