Highly enantioselective synthesis of multifunctionalized allylic building blocks via oxazaborolidine-catalyzed borane reduction

被引:11
作者
Cho, BT [1 ]
Shin, SH [1 ]
机构
[1] Hallym Univ, Dept Chem, Chunchon 200702, South Korea
关键词
asymmetric reduction; oxazaborolidine-catalyzed reduction; chiral alkenyl beta-hydroxy sulfides; dianion alkylation; chiral alpha; beta-unsaturated diol;
D O I
10.1016/j.tet.2005.05.018
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and convenient synthesis of optically active alkenyl beta-hydroxy sulfides with high enantiomeric excess by CBS-oxazaborolidine-catalyzed borane reduction of the corresponding beta-keto sulfides and its application to synthesis of chiral alkenic diols have been established. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6959 / 6966
页数:8
相关论文
共 63 条
[1]   Enantioselective epoxidation with chiral MnIII(salen) catalysts:: Kinetic resolution of aryl-substituted allylic alcohols [J].
Adam, W ;
Humpf, HU ;
Roschmann, KJ ;
Saha-Möller, CR .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (17) :5796-5800
[2]  
Aleu J, 2000, EUR J ORG CHEM, V2000, P3031
[3]   Synthesis and reactivity of enantiomerically pure 2-fluoromethyl-2-(1′-p-tolylsulfinyl)alkyl oxiranes [J].
Arnone, A ;
Bravo, P ;
Frigerio, M ;
Viani, F ;
Soloshonok, VA .
TETRAHEDRON, 1998, 54 (39) :11825-11840
[4]   A SYNTHETIC APPROACH TOWARDS OCTALACTIN-A, BASED ON THE STEREOSELECTIVE REDUCTION OF ALPHA,BETA-UNSATURATED KETONES [J].
BACH, J ;
BERENGUER, R ;
GARCIA, J ;
VILARRASA, J .
TETRAHEDRON LETTERS, 1995, 36 (19) :3425-3428
[5]   SYNTHESIS OF THE (4S,5R)-5-HYDROXY-DECAN-4-OLIDE (L-FACTOR) AND OF THE (R)-DECAN-4-OLIDE FROM A CHIRAL SULFOXIDE [J].
BRAVO, P ;
RESNATI, G ;
VIANI, F ;
ARNONE, A .
TETRAHEDRON, 1987, 43 (20) :4635-4647
[6]  
Brenna E, 2001, EUR J ORG CHEM, V2001, P1349
[7]   ASYMMETRIC-SYNTHESIS OF CYCLOHEX-2-ENOLS - THE EXAMPLES OF SEUDENOL AND ANALOGS [J].
BUENO, AB ;
CARRENO, MC ;
RUANO, JLG ;
HAMDOUCHI, C .
TETRAHEDRON-ASYMMETRY, 1995, 6 (06) :1237-1240
[8]   APPLICATIONS OF SULFOXIDES TO ASYMMETRIC-SYNTHESIS OF BIOLOGICALLY-ACTIVE COMPOUNDS [J].
CARRENO, MC .
CHEMICAL REVIEWS, 1995, 95 (06) :1717-1760
[9]   ACYCLIC STEREOCONTROL INDUCED BY ALLYLIC ALKOXY GROUPS - SYNTHETIC APPLICATIONS OF STEREOSELECTIVE DIHYDROXYLATION IN NATURAL PRODUCT SYNTHESIS [J].
CHA, JK ;
KIM, NS .
CHEMICAL REVIEWS, 1995, 95 (06) :1761-1795
[10]  
CHANDRASEKHAR S, 1995, TETRAHEDRON LETT, V36, P5071