Calixpyrrole Derivatives: "Multi Hydrogen Bond" Catalysts for γ-Butenolide Synthesis

被引：25

作者：

Cafeo, Grazia ^{[1
]}

De Rosa, Margherita ^{[2
]}

Kohnke, Franz H. ^{[1
]}

Soriente, Annunziata ^{[2
]}

Talotta, Carmen ^{[2
]}

Valenti, Luca ^{[1
]}

机构：

[1] Univ Messina, Dept Organ & Biol Chem, I-98166 Messina, Italy

[2] Univ Salerno, Dept Chem, I-84084 Fisciano, SA, Italy

来源：

MOLECULES | 2009年 / 14卷 / 07期

关键词：

calixpyrroles; diastereoselective synthesis; organocatalysis; aldol addition; 2-Trimethyl-silyloxyfuran; EFFICIENT TOTAL-SYNTHESIS; ANION-BINDING PROPERTIES; ALDOL REACTION; ORGANOCATALYSIS; 2-TRIMETHYLSILYLOXYFURAN; MUKAIYAMA; UREA;

D O I：

10.3390/molecules14072594

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Calix[4]pyrrole (1), calix[2]m-benzo[4]pyrrole (2), 10 alpha,20 beta- and 10 alpha,20 alpha-bis(4-nitrophenyl)-calix[4]pyrroles 3 and 4, respectively, were found to exhibit various organocatalytic activities in the diastereoselective vinylogous addition reaction of 2-trimethylsilyloxyfuran (TMSOF, 7) to aldehydes. The gamma-hydroxybutenolide products are obtained in fairly good yields and with moderate diastereoselectivity. The structures of the catalysts, as well as the reaction conditions, strongly influence the efficiency of the reaction.

引用

页码：2594 / 2601

页数：8

共 39 条

[1] Silicon tetrachloride in organic synthesis: new applications for the vinylogous aldol reaction [J].

Acocella, MR ;

De Rosa, M ;

Massa, A ;

Palombi, L ;

Villano, R ;

Scettri, A .

TETRAHEDRON, 2005, 61 (16) :4091-4097

[2] Recent progress in chiral Bronsted acid catalysis [J].

Akiyama, Takahiko ;

Itoh, Junji ;

Fuchibe, Kohei .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010

[3] Facile access to 4-aryl-2(5H)-furanones by Suzuki cross coupling:: Efficient synthesis of rubrolides C and E [J].

Boukouvalas, J ;

Lachance, N ;

Ouellet, M ;

Trudeau, M .

TETRAHEDRON LETTERS, 1998, 39 (42) :7665-7668

[4] AN EFFICIENT TOTAL SYNTHESIS OF NEOPATULIN [J].

BOUKOUVALAS, J ;

MALTAIS, F .

TETRAHEDRON LETTERS, 1994, 35 (32) :5769-5770

[5] AN EFFICIENT TOTAL SYNTHESIS OF THE ANTIBIOTIC PATULIN [J].

BOUKOUVALAS, J ;

MALTAIS, F .

TETRAHEDRON LETTERS, 1995, 36 (40) :7175-7176

[6]

BOUKOUVALAS J, 1994, TETRAHEDRON LETT, V35, P7897, DOI 10.1016/S0040-4039(00)78379-1

[7] REGIOSTEREOSELECTIVITY AND DIASTEREOSELECTIVITY IN ALDOL REACTIONS OF CYCLOPENT-2-ENONE, 2-(5H)FURANONE AND THEIR DERIVED TRIMETHYLSILYLOXYDIENES [J].

BROWN, DW ;

CAMPBELL, MM ;

TAYLOR, AP ;

ZHANG, X .

TETRAHEDRON LETTERS, 1987, 28 (09) :985-988

[8] The first enantioselective organocatalytic Mukaiyama- Michael reaction:: A direct method for the synthesis of enantioenriched γ-butenolide architecture [J].

Brown, SP ;

Goodwin, NC ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (05) :1192-1194

[9] Tuning the anion binding properties of calixpyrroles by means of p-nitrophenyl substituents at their meso-positions [J].

Bruno, Giuseppe ;

Cafeo, Grazia ;

Kohnke, Franz H. ;

Nicolo, Francesco .

TETRAHEDRON, 2007, 63 (40) :10003-10010

[10] Efficient organocatalysis with a calix[4]pyrrole derivative [J].

Cafeo, Grazia ;

De Rosa, Margherita ;

Kohnke, Franz H. ;

Neri, Placido ;

Soriente, Annunziata ;

Valenti, Luca .

TETRAHEDRON LETTERS, 2008, 49 (01) :153-155

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