Rhodium-Catalyzed Synthesis of 3-Hydroxy-β-lactams via Oxonium Ylide Generation: Three-Component Reaction between Azetidine-2,3-diones, Ethyl Diazoacetate, and Alcohols

被引：22
作者：
Alcaide, Benito [1 ]
Almendros, Pedro [2 ]
Aragoncillo, Cristina [1 ]
Callejo, Ricardo [1 ]
Pilar Ruiz, M. [1 ]
Rosario Torres, M. [3 ]
机构：
[1] Univ Complutense, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
[2] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
[3] Univ Complutense, Fac Quim, Lab Difracc Rayos X, E-28040 Madrid, Spain
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 21期
关键词：
DIAZO-COMPOUNDS; BETA-LACTAM; GLUTAMINE-SYNTHETASE; ORGANIC-SYNTHESIS; MECHANISM; REARRANGEMENT; TABTOXININE; OLEFINATION; CYCLIZATION; INHIBITOR;
D O I：
10.1021/jo9019013
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
3-Substituted-3-hydroxy-beta-lactsms, with two new adjacent stereogenic centers, have been prepared in it single step by a rhodium-catalyzed, three-component reaction between azeticime-2,3-diones, ethyl diazoacetate, and alcohols. Good to moderate stereoselectivity was obtained depending on the alcohol used. The stercochemistry of the new centers has been undoubtedly assigned by single crystal X-ray diffraction.
引用
收藏
页码：8421 / 8424
页数：4
相关论文
共 46 条
[1]   Generation of phosphoranes derived from phosphites.: A new class of phosphorus ylides leading to high E selectivity with semi-stabilizing groups in Wittig olefinations [J].
Aggarwal, VK ;
Fulton, JR ;
Sheldon, CG ;
de Vicente, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (20) :6034-6035
[2]   Metal-promoted allylation, propargylation, or allenylation of azetidine-2,3-diones in aqueous and anhydrous media.: Application to the asymmetric synthesis of densely functionalized 3-substituted 3-hydroxy-β-lactams [J].
Alcaide, B ;
Almendros, P ;
Aragoncillo, C ;
Rodríguez-Acebes, R .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (15) :5208-5216
[3]   Recent progress in the synthesis and reactivity of azetidine-2,3-diones. A review [J].
Alcaide, B ;
Almendros, P .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2001, 33 (04) :315-+
[4]   New regiocontrolled synthesis of functionalized pyrroles from 2-azetidinone-tethered allenols [J].
Alcaide, Benito ;
Almendros, Pedro ;
Carrascosa, Rocio ;
Redondo, Maria C. .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (02) :637-643
[5]   Direct organocatalytic synthesis of enantiopure succinimides from β-lactam aldehydes through ring expansion promoted by azolium salt precatalysts [J].
Alcaide, Benito ;
Almendros, Pedro ;
Cabrero, Gema ;
Ruiz, M. Pilar .
CHEMICAL COMMUNICATIONS, 2007, (45) :4788-4790
[6]   Metal-catalyzed regiodivergent cyclization of γ-allenols:: Tetrahydrofurans versus oxepanes [J].
Alcaide, Benito ;
Almendros, Pedro ;
del Campo, Teresa Martinez .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (35) :6684-6687
[7]   Diversity-oriented preparation of enantiopure spirocyclic 2-azetidinones from α-oxo-β-lactams through barbier-type reactions followed by metal-catalyzed cyclizations [J].
Alcaide, Benito ;
Almendros, Pedro ;
Martinez del Campo, Teresa ;
Rodriguez-Acebes, Raquel .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (4-5) :749-758
[8]   Indium-promoted acyloxyallylation reaction of azetidine-2,3-diones in aqueous media:: A new route to densely functionalized 3-substituted 3-hydroxy-β-lactams [J].
Alcaide, Benito ;
Almendros, Pedro ;
Aragoncillo, Cristina ;
Cabrero, Gema ;
Callejo, Ricardo ;
Ruiz, M. Pilar .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (26) :4434-4439
[9]   Synthesis of Spiroheterocycles by Palladium-Catalyzed Domino Cycloisomerization/Cross-Coupling of α-Allenols and Baylis-Hillman Acetates [J].
Alcaide, Benito ;
Almendros, Pedro ;
Martinez del Campo, Teresa ;
Teresa Quiros, M. .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (14) :3344-3346
[10]   SYNTHETIC STUDIES ON TABTOXIN - SYNTHESIS OF A NATURALLY-OCCURRING INHIBITOR OF GLUTAMINE-SYNTHETASE, TABTOXININE-BETA-LACTAM, AND ANALOGS [J].
BALDWIN, JE ;
OTSUKA, M ;
WALLACE, PM .
TETRAHEDRON, 1986, 42 (12) :3097-3110
12345