Highly Enantioselective One-Pot Synthesis of Chiral β-Hydroxy Sulfones via Asymmetric Transfer Hydrogenation in an Aqueous Medium

被引：36

作者：

Zhang, Dacheng ^{[1
]}

Cheng, Tanyu ^{[1
]}

Zhao, Qiankun ^{[1
]}

Xu, Jianyou ^{[1
]}

Liu, Guohua ^{[1
]}

机构：

[1] Shanghai Normal Univ, Key Lab Resource Chem, Shanghai Key Lab Rare Earth Funct Mat, Minist Educ, Shanghai 200234, Peoples R China

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 21期

关键词：

BAKERS-YEAST REDUCTION; KETO-SULFONES; CASCADE REACTIONS; EFFICIENT SYNTHESIS; AROMATIC KETONES; CATALYSIS; LIGANDS; WATER; BUTENOLIDES; RESOLUTION;

D O I：

10.1021/ol502832a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild transformation in an aqueous medium for the one-pot synthesis of optically active beta-hydroxy sulfones is described. The intermediates of beta-keto sulfones obtained via a nucleophilic substitution reaction of alpha-bromoketones and sodium sulfinates in H2O/MeOH (1:3, v/v) at 50 degrees C were reduced through Ru-catalyzed asymmetric transfer hydrogenation in one-pot using HCOONa as a hydrogen source providing a variety of chiral beta-hydroxy sulfones with high yields and excellent enantioselectivities.

引用

收藏

页码：5764 / 5767

页数：4

相关论文

共 60 条

[51] Accelerated asymmetric transfer hydrogenation of aromatic ketones in water [J].

Wu, XF ;

Li, XG ;

Hems, W ;

King, F ;

Xiao, JL .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (13) :1818-1821

[52] Catalytic Cascade Reactions Involving Metal Carbene Migratory Insertion [J].

Xia, Ying ;

Zhang, Yan ;

Wang, Jianbo .

ACS CATALYSIS, 2013, 3 (11) :2586-2598

[53] A bifunctionalized organic-inorganic hybrid silica: synergistic effect enhances enantioselectivity [J].

Xiao, Wei ;

Jin, Ronghua ;

Cheng, Tanyu ;

Xia, Daquan ;

Yao, Hui ;

Gao, Fei ;

Deng, Boxin ;

Liu, Guohua .

CHEMICAL COMMUNICATIONS, 2012, 48 (97) :11898-11900

[54] Homochiral Metal-Organic Frameworks for Asymmetric Heterogeneous Catalysis [J].

Yoon, Minyoung ;

Srirambalaji, Renganathan ;

Kim, Kimoon .

CHEMICAL REVIEWS, 2012, 112 (02) :1196-1231

[55] Recent developments in asymmetric transfer hydrogenation with Hantzsch esters: A biomimetic approach [J].

You, Shu-Li .

CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (07) :820-827

[56] ASYMMETRIC HYDROGEN TRANSFER-REACTIONS PROMOTED BY HOMOGENEOUS TRANSITION-METAL CATALYSTS [J].

ZASSINOVICH, G ;

MESTRONI, G ;

GLADIALI, S .

CHEMICAL REVIEWS, 1992, 92 (05) :1051-1069

[57] Enantio-Relay Catalysis Constructs Chiral Biaryl Alcohols over Cascade Suzuki Cross-Coupling-Asymmetric Transfer Hydrogenation [J].

Zhang, Dacheng ;

Gao, Xiaoshuang ;

Cheng, Tanyu ;

Liu, Guohua .

SCIENTIFIC REPORTS, 2014, 4

[58] Synthesis of a biferrocene diphosiphine ligand with only planar chirality and its application in the Rh-catalyzed asymmetric hydrogenation of β-keto sulfones [J].

Zhang, Hui-Li ;

Hou, Xue-Long ;

Dai, Li-Xin ;

Luo, Zhi-Bin .

TETRAHEDRON-ASYMMETRY, 2007, 18 (02) :224-228

[59] Enantioselective reduction of β-keto sulfones using the NaBH4/Me3SiCl system catalyzed by polymer-supported chiral sulfonamide [J].

Zhao, G ;

Hu, JB ;

Qian, ZS ;

Yin, WX .

TETRAHEDRON-ASYMMETRY, 2002, 13 (19) :2095-2098

[60] Recent Advances on the Lewis Acid-Catalyzed Cascade Rearrangements of Propargylic Alcohols and Their Derivatives [J].

Zhu, Yuanxun ;

Sun, Lang ;

Lu, Ping ;

Wang, Yanguang .

ACS CATALYSIS, 2014, 4 (06) :1911-1925

← 1 2 3 4 5 6 →