Highly efficient synthesis of chiral β-hydroxy sulfides with high enantiomeric purity via CBS-oxazaborolidine-catalyzed borane reduction

被引：24

作者：

Cho, BT ^{[1
]}

Choi, OK ^{[1
]}

Kim, DJ ^{[1
]}

机构：

[1] Hallym Univ, Dept Chem, Chunchon 200702, South Korea

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 07期

基金：

新加坡国家研究基金会;

关键词：

D O I：

10.1016/S0957-4166(02)00193-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A simple and efficient synthesis of chiral beta-hydroxy p-tolylsulfides with high enantiomeric purity by CBS-oxazaborolidine-catalyzed asymmetric borane reduction of beta-keto p-tolyisulfides using N-ethyl-N-isopropylaniline-borane complex as the borane carrier is reported. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：697 / 703

页数：7

相关论文

共 57 条

[1] 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

[2] 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

[3] APPLICATIONS OF SULFOXIDES TO ASYMMETRIC-SYNTHESIS OF BIOLOGICALLY-ACTIVE COMPOUNDS [J].

CARRENO, MC .

CHEMICAL REVIEWS, 1995, 95 (06) :1717-1760

[4]

Cho B. T., 2001, ACS SYM SER, V783, P122

[5] Catalytic enantioselective reactions.: Part 16.: Oxazaborolidine-catalyzed asymmetric borane reduction of α-keto acetals [J].

Cho, BT ;

Chun, YS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (15) :2095-2100

[6] Facile synthesis of terminal 1,2-diols with high optical purity via oxazaborolidine-catalyzed asymmetric borane reduction [J].

Cho, BT ;

Chun, YS .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (15) :5280-5282

[7] A practical method for synthesis of terminal 1,2-diols in high enantiomeric excess via oxazaborolidine-catalyzed asymmetric reduction [J].

Cho, BT ;

Chun, YS .

TETRAHEDRON-ASYMMETRY, 1999, 10 (10) :1843-1846

[8] Efficient synthesis of optically active β-hydroxy p-tolylsulfones with very high enantiomeric excess via CBS-oxazaborolidine-catalyzed borane reduction [J].

Cho, BT ;

Kim, DJ .

TETRAHEDRON-ASYMMETRY, 2001, 12 (14) :2043-2047

[9] Convenient synthesis of optically active 1,2-diol monosulfonates and terminal epoxides via oxazaborolidine-catalyzed asymmetric borane reduction of α-sulfonyloxy ketones [J].

Cho, BT ;

Yang, WK ;

Choi, OK .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (10) :1204-1211

[10] A convenient synthesis of (1S,2R)-1,2-indene oxide and trans-(1S,2S)-2-bromo-1-indanol via oxazaborolidine-catalyzed borane reduction [J].

Choi, OK ;

Cho, BT .

TETRAHEDRON-ASYMMETRY, 2001, 12 (06) :903-907

← 1 2 3 4 5 6 →