Highly efficient asymmetric aldol reaction in brine using a fluorous sulfonamide organocatalyst

被引：24

作者：

Miura, Tsuyoshi ^{[1
]}

Kasuga, Hikaru ^{[1
]}

Imai, Kie ^{[1
]}

Ina, Mariko ^{[1
]}

Tada, Norihiro ^{[1
]}

Imai, Nobuyuki ^{[2
]}

Itoh, Akichika ^{[1
]}

机构：

[1] Gifu Pharmaceut Univ, Gifu 5011196, Japan

[2] Chiba Inst Sci, Fac Pharm, Choshi, Chiba 2880025, Japan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 11期

关键词：

WATER-COMPATIBLE ORGANOCATALYSTS; MICHAEL ADDITION-REACTIONS; DIELS-ALDER REACTIONS; CHIRAL PRIMARY AMINE; DIRECT SYN-ALDOL; ORGANIC-REACTIONS; AQUEOUS-MEDIA; ALIPHATIC-KETONES; SMALL PEPTIDES; ALDEHYDES;

D O I：

10.1039/c2ob06955e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A fluorous organocatalyst promotes direct asymmetric aldol reactions of aromatic aldehydes with ketones in brine to afford the corresponding anti-aldol products in high yield with up to 96% ee. Fluorous organocatalyst can be readily recovered by solid phase extraction using fluorous silica gel and reused without purification.

引用

收藏

页码：2209 / 2213

页数：5

相关论文

共 94 条

[1] Simple amphiphilic isosteviol-proline conjugates as chiral catalysts for the direct asymmetric aldol reaction in the presence of water [J].

An, Ya-Jie ;

Zhang, Yun-Xiao ;

Wu, Ya ;

Liu, Zhao-Min ;

Pi, Chao ;

Tao, Jing-Chao .

TETRAHEDRON-ASYMMETRY, 2010, 21 (06) :688-694

[2] Small organic molecule in enantioselective, direct aldol reaction "in water'' [J].

Aratake, Seiji ;

Itoh, Takahiko ;

Okano, Tsubasa ;

Usui, Takahiro ;

Shoji, Mitsuru ;

Hayashi, Yujiro .

CHEMICAL COMMUNICATIONS, 2007, (24) :2524-2526

[3] Developing Novel Organocatalyzed Aldol Reactions for the Enantioselective Synthesis of Biologically Active Molecules [J].

Bhanushali, Mayur ;

Zhao, Cong-Gui .

SYNTHESIS-STUTTGART, 2011, (12) :1815-1830

[4] The role of double hydrogen bonds in asymmetric direct aldol reactions catalyzed by amino amide derivatives [J].

Chen, Xiao-Hua ;

Yu, Jie ;

Gong, Liu-Zhu .

CHEMICAL COMMUNICATIONS, 2010, 46 (35) :6437-6448

[5] Protonated chiral prolinamide catalyzed enantioselective direct aldol reaction in water [J].

Chimni, SS ;

Mahajan, D ;

Babu, VVS .

TETRAHEDRON LETTERS, 2005, 46 (34) :5617-5619

[6] The pH of the reaction controls the stereoselectivity of organocatalyzed direct aldol reactions in water [J].

Chimni, Swapandeep Singh ;

Singh, Sarbjit ;

Kumar, Akshay .

TETRAHEDRON-ASYMMETRY, 2009, 20 (15) :1722-1724

[7] Protonated (S)-prolinamide derivatives-water compatible organocatalysts for direct asymmetric aldol reaction [J].

Chimni, Swapandeep Singh ;

Singh, Sarbjit ;

Mahajan, Dinesh .

TETRAHEDRON-ASYMMETRY, 2008, 19 (19) :2276-2284

[8] CBS reductions with a fluorous prolinol immobilized in a hydrofluoroether solvent [J].

Chu, Qianli ;

Yu, Marvin S. ;

Curran, Dennis P. .

ORGANIC LETTERS, 2008, 10 (05) :749-752

[9] A recyclable fluorous organocatalyst for Diels-Alder reactions [J].

Chu, Qianli ;

Zhang, Wei ;

Curran, Dennis P. .

TETRAHEDRON LETTERS, 2006, 47 (52) :9287-9290

[10] Acyclic amino acid-catalyzed direct asymmetric aldol reactions:: alanine, the simplest stereoselective organocatalyst [J].

Córdova, A ;

Zou, WB ;

Ibrahem, I ;

Reyes, E ;

Engqvist, M ;

Liao, WW .

CHEMICAL COMMUNICATIONS, 2005, (28) :3586-3588

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