Synthesis of Indenes by Intramolecular Morita-Baylis-Hillman Reaction in Aqueous Media Catalyzed by Resin-Supported Proline

被引:21
作者
Akagawa, Kengo [1 ]
Sakamoto, Seiji [1 ]
Kudo, Kazuaki [1 ]
机构
[1] Univ Tokyo, Inst Ind Sci, Meguro Ku, Tokyo 1538505, Japan
关键词
supported catalysis; annulation; aldehydes; proline; Morita-Baylis-Hillman reaction; ASYMMETRIC TRANSFER HYDROGENATION; EFFICIENT SYNTHESIS; FUNCTIONALIZED INDENES; RADICAL CYCLIZATION; RATE ACCELERATION; PEPTIDE CATALYST; AROMATIC KETONES; TANDEM REACTIONS; 3+2 ANNULATION; ALKYNES;
D O I
10.1055/s-0030-1259683
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Novel synthesis of indene derivatives has been developed in an organocatalytic way. Although homogeneous proline showed low catalytic efficiency, resin-supported proline effectively catalyzed the intramolecular Morita-Baylis-Hillman reaction to afford the desired indenes.
引用
收藏
页码:817 / 820
页数:4
相关论文
共 100 条
[1]   Rate acceleration of the Baylis-Hillman reaction in polar solvents (water and formamide). Dominant role of hydrogen bonding, not hydrophobic effects, is implicated [J].
Aggarwal, VK ;
Dean, DK ;
Mereu, A ;
Williams, R .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (02) :510-514
[2]   Direct asymmetric aldol reaction in aqueous media using polymer-supported peptide [J].
Akagawa, K ;
Sakamoto, S ;
Kudo, K .
TETRAHEDRON LETTERS, 2005, 46 (47) :8185-8187
[3]   Organocatalytic asymmetric transfer hydrogenation in aqueous media using resin-supported peptide having a polyleucine tether [J].
Akagawa, Kengo ;
Akabane, Hajime ;
Sakamoto, Seiji ;
Kudo, Kazuaki .
ORGANIC LETTERS, 2008, 10 (10) :2035-2037
[4]   Resin-supported acid- and base-catalyzed one-pot sequential reaction including an enantioselective step [J].
Akagawa, Kengo ;
Sakamoto, Seiji ;
Kudo, Kazuaki .
TETRAHEDRON LETTERS, 2007, 48 (06) :985-987
[5]   One-pot sequential alcohol oxidation and asymmetric α-oxyamination in aqueous media using recyclable resin-supported peptide catalyst [J].
Akagawa, Kengo ;
Fujiwara, Takuma ;
Sakamoto, Seiji ;
Kudo, Kazuaki .
CHEMICAL COMMUNICATIONS, 2010, 46 (42) :8040-8042
[6]   Efficient Asymmetric α-Oxyamination of Aldehydes by Resin-Supported Peptide Catalyst in Aqueous Media [J].
Akagawa, Kengo ;
Fujiwara, Takuma ;
Sakamoto, Seiji ;
Kudo, Kazuaki .
ORGANIC LETTERS, 2010, 12 (08) :1804-1807
[7]   Friedel-Crafts-type alkylation in aqueous media using resin-supported peptide catalyst having polyleucine [J].
Akagawa, Kengo ;
Yamashita, Takuhiro ;
Sakamoto, Seiji ;
Kudo, Kazuaki .
TETRAHEDRON LETTERS, 2009, 50 (40) :5602-5604
[8]   Asymmetric transfer hydrogenation in aqueous media catalyzed by resin-supported peptide having a polyleucine tether [J].
Akagawa, Kengo ;
Akabane, Hajime ;
Sakamoto, Seiji ;
Kudo, Kazuaki .
TETRAHEDRON-ASYMMETRY, 2009, 20 (04) :461-466
[9]   "Microencapsulated" and Related Catalysts for Organic Chemistry and Organic Synthesis [J].
Akiyama, Ryo ;
Kobayashi, Shu .
CHEMICAL REVIEWS, 2009, 109 (02) :594-642
[10]   Indene-based scaffolds. Design and synthesis of novel serotonin 5-HT6 receptor ligands [J].
Alcalde, Ermitas ;
Mesquida, Neus ;
Frigola, Jordi ;
Lopez-Perez, Sara ;
Merce, Ramon .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (20) :3795-3810