Journal of Organic Chemistry 2009-11-06

Rhodium-catalyzed synthesis of 3-hydroxy-beta-lactams via oxonium ylide generation: three-component reaction between azetidine-2,3-diones, ethyl diazoacetate, and alcohols.

Benito Alcaide, Pedro Almendros, Cristina Aragoncillo, Ricardo Callejo, M Pilar Ruiz, M Rosario Torres

Index: J. Org. Chem. 74(21) , 8421-4, (2009)

Full Text: HTML

Abstract

3-Substituted-3-hydroxy-beta-lactams, with two new adjacent stereogenic centers, have been prepared in a single step by a rhodium-catalyzed, three-component reaction between azetidine-2,3-diones, ethyl diazoacetate, and alcohols. Good to moderate stereoselectivity was obtained depending on the alcohol used. The stereochemistry of the new centers has been undoubtedly assigned by single crystal X-ray diffraction.

Related Compounds

  • EDA

Related Articles:

Design of a Heterogeneous Catalyst Based on Cellulose Nanocrystals for Cyclopropanation: Synthesis and Solid-State NMR Characterization.

2015-08-24

[Chemistry 21 , 12414-20, (2015)]

Silver-catalyzed vinylogous fluorination of vinyl diazoacetates.

2013-12-20

[Org. Lett. 15(24) , 6152-4, (2013)]

An efficient and convenient synthesis of ethyl 1-(4-methoxyphenyl)-5-phenyl-1H-1,2,3-triazole-4-carboxylate.

2010-02-01

[Chem. Asian J. 5(2) , 328-33, (2010)]

Component match in rhodium catalyzed three-component reactions of ethyl diazoacetate, H2O and aryl imines: a highly diastereoselective one-step synthesis of beta-aryl isoserine derivatives.

2009-12-07

[Org. Biomol. Chem. 7(23) , 5028-33, (2009)]

Palladium-catalyzed cross-coupling of aryl or vinyl iodides with ethyl diazoacetate.

2007-07-18

[J. Am. Chem. Soc. 129(28) , 8708-9, (2007)]

More Articles...