Darzens Reaction of Acyl Phosphonates with α-Bromo Ketones: Selective Synthesis of cis-and trans-Epoxyphosphonates

AS Demir, M Emrullahoglu, E Pirkin…

Index: Demir, Ayhan S.; Emrullahoglu, Mustafa; Pirkin, Eser; Akca, Nazmiye Journal of Organic Chemistry, 2008 , vol. 73, # 22 p. 8992 - 8997

Full Text: HTML

Citation Number: 15

Abstract

Acyl phosphonates with α-halo ketones in the presence of bases at room temperature afford cis-and trans-epoxyphosphonates in good chemical yields and high selectivities using different bases. The diastereoselectivity of this reaction is easily controlled by changing the base. Changing the base from Cs2CO3 to DBU changed the diastereomeric ratio (trans/cis) from 3/2 to 9/1. Moreover, the treatment of the trans isomer with DBU showed a complete ...

Related Articles:

Enantioselective synthesis of α-tertiary hydroxyaldehydes by palladium-catalyzed asymmetric allylic alkylation of enolates

[Trost, Barry M.; Xu, Jiayi; Reichle, Markus Journal of the American Chemical Society, 2007 , vol. 129, # 2 p. 282 - 283]

N-Heterocyclic carbene catalyzed regioselective oxo-acyloxylation of alkenes with aromatic aldehydes: a high yield synthesis of α-acyloxy ketones and esters

[Reddi, Rambabu N.; Malekar, Pushpa V.; Sudalai, Arumugam Organic and Biomolecular Chemistry, 2013 , vol. 11, # 38 p. 6477 - 6482]

A Convenient and Versatile Method for the Preparation of α??Hydroxymethyl Ketone Derivatives from the Corresponding Allyl Silyl Ethers or Allyl Carboxylates

[Hon, Yung-Son; Wong, Ying-Chieh; Wu, Kuo-Jui Journal of the Chinese Chemical Society, 2008 , vol. 55, # 4 p. 896 - 914]

One-pot synthesis of phenacyl esters from acetophenone,[Bmim] Br3, and potassium salts of carboxylic acids under solvent-free conditions

[Le, Zhang-Gao; Xie, Zong-Bo; Xu, Jian-Ping Synthetic Communications, 2009 , vol. 39, # 4 p. 743 - 747]

Electrochemical Carboxylation of N-(2-Bromopropionyl)-4 R-phenyloxazolidin-2-one: An Efficient Route to Unsymmetrical Methylmalonic Ester Derivatives

[Carelli, Italo; Curulli, Antonella; Inesi, Achille; Zeuli, Errico Journal of Chemical Research, Miniprint, 1988 , # 5 p. 1276 - 1296]

More Articles...