A heterobimetallic Pd/La/Schiff base complex for anti-selective catalytic asymmetric nitroaldol reactions and applications to short syntheses of β-adrenoceptor agonists

被引：168

作者：

Handa, Shinya ^{[1
]}

Nagawa, Keita ^{[1
]}

Sohtome, Yoshihiro ^{[1
]}

Matsunaga, Shigeki ^{[1
]}

Shibasaki, Masakatsit ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 17期

关键词：

agonists; amino alcohols; asymmetric catalysis; nitroaldol reaction;

D O I：

10.1002/anie.200705617

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Two metals in a pod: The combination of Pd and La with a dinucleating Schiff base was developed for anti selectivity in the catalytic asymmetric nitroaldol reaction (see scheme). Short syntheses of β-adrenoceptor agonists by using the heterobimetallic catalyst are presented. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：3230 / 3233

页数：4

共 59 条

[1] Synthesis and biological evaluation of analogues of the anti-tumor alkaloid naamidine A [J].

Aberle, Nicholas ;

Catime, Jenny ;

Nice, Edouard C. ;

Watson, Keith G. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (13) :3741-3744

[2] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].

Ager, DJ ;

Prakash, I ;

Schaad, DR .

CHEMICAL REVIEWS, 1996, 96 (02) :835-875

[3] Catalysis of the Michael addition reaction by late transition metal complexes of BINOL-derived salens [J].

Annamalai, V ;

DiMauro, EF ;

Carroll, PJ ;

Kozlowski, MC .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) :1973-1981

[4]

[Anonymous], 2004, MULTIMETALLIC CATALY

[5]

Arai T., 2006, ANGEW CHEM, V118, P6124

[6] Practical asymmetric henry reaction catalyzed by a chiral Diamine-Cu(OAc)2 complex [J].

Arai, Takayoshi ;

Watanabe, Masahiko ;

Yanagisawa, Akira .

ORGANIC LETTERS, 2007, 9 (18) :3595-3597

[7] 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

[8] Recoverable PEG-supported copper catalyst for highly stereocontrolled nitroaldol condensation [J].

Bandini, Marco ;

Benaglia, Maurizio ;

Sinisi, Riccardo ;

Tommasi, Simona ;

Umani-Ronchi, Achille .

ORGANIC LETTERS, 2007, 9 (11) :2151-2153

[9] 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

[10] The synthesis of vicinal amino alcohols [J].

Bergmeier, SC .

TETRAHEDRON, 2000, 56 (17) :2561-2576

← 1 2 3 4 5 6 →