Recoverable PEG-supported copper catalyst for highly stereocontrolled nitroaldol condensation

被引：91

作者：

Bandini, Marco

Benaglia, Maurizio

Sinisi, Riccardo

Tommasi, Simona

Umani-Ronchi, Achille

机构：

[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

[2] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 11期

关键词：

D O I：

10.1021/ol070636w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new poly(ethylene glycol)-modified DAT2-Cu(OAc)(2) complex smoothly catalyzes a base-free nitroaldol condensation in a highly enantioselective manner (ee up to 93%) also in reagent-grade solvent and in the presence of air. Effective recovery and recycling (up to five runs) of supported catalysts are documented.

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收藏

页码：2151 / 2153

页数：3

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共 36 条

[1] Controlling stereochemical outcomes of asymmetric processes by catalyst remote molecular functionalizations: Chiral diamino-oligothiophenes (DATs) as ligands in asymmetric catalysis [J].

Albano, VG ;

Bandini, M ;

Barbarella, G ;

Melucci, M ;

Monari, M ;

Piccinelli, F ;

Tommasi, S ;

Umani-Ronchi, A .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (03) :667-675

[2] Novel chiral diamino-oligothiophenes as valuable ligands in Pd-catalyzed allylic alkylations. On the "primary" role of "secondary" interactions in asymmetric catalysis [J].

Albano, VG ;

Bandini, M ;

Melucci, M ;

Monari, M ;

Piccinelli, F ;

Tommasi, S ;

Umani-Ronchi, A .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1507-1512

[3] Synthesis, structural characterization, and catalytic activity of chiral diamine and diimine Pd(II)-complexes [J].

Albano, Vincenzo Giulio ;

Bandini, Marco ;

Monari, Magda ;

Piccinelli, Fabio ;

Tommasi, Simona ;

Umani-Ronchi, Achille .

INORGANICA CHIMICA ACTA, 2007, 360 (03) :1000-1008

[4] Poly(ethylene glycol)-supported bisoxazolines as ligands for catalytic enantioselective synthesis [J].

Annunziata, R ;

Benaglia, M ;

Cinquini, M ;

Cozzi, F ;

Pitillo, M .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (09) :3160-3166

[5] Direct monitoring of the asymmetric induction of solid-phase catalysis using circular dichroism:: Diamine-CuI-catalyzed asymmetric Henry reaction [J].

Arai, Takayoshi ;

Watanabe, Masahiko ;

Fujiwara, Akitsugu ;

Yokoyama, Naota ;

Yanagisawa, Akira .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (36) :5978-5981

[6] Highly enantioselective nitroaldol reaction catalyzed by new chiral copper complexes [J].

Bandini, Marco ;

Piccinelli, Fabio ;

Tommasi, Simona ;

Umani-Ronchi, Achille ;

Ventrici, Caterina .

CHEMICAL COMMUNICATIONS, 2007, (06) :616-618

[7] New recoverable poly(ethylene glycol)-supported C1-diamino-oligothiophene ligands for palladium-promoted asymmetric allylic alkylation (AAA) reactions [J].

Bandini, Marco ;

Benaglia, Maurizio ;

Quinto, Tommaso ;

Tommasi, Simona ;

Umani-Ronchi, Achille .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (12-13) :1521-1527

[8] Enantioselective catalysis in water: Mukaiyama-aldol condensation promoted by copper complexes of bisoxazolines supported on poly(ethylene glycol) [J].

Benaglia, M ;

Cinquini, M ;

Cozzi, F ;

Celentano, G .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (22) :3401-3407

[9] Polymer-supported organic catalysts [J].

Benaglia, M ;

Puglisi, A ;

Cozzi, F .

CHEMICAL REVIEWS, 2003, 103 (09) :3401-3429

[10] Synthesis of poly(ethylene glycol)-supported manganese porphyrins: efficient, recoverable and recyclable catalysts for epoxidation of alkenes [J].

Benaglia, M ;

Danelli, T ;

Pozzi, G .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (03) :454-456

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