Regioselectivity in the Reaction of Ethyl Diethoxyphosphorylacetate with 1-Aryl-2-haloalkan-1-ones: Effective Synthesis of 4-Aryl-2-diethoxyphosphoryl-4-oxobutanoates

Abstract

The regioselectivity of the reaction of ethyl diethoxyphosphorylacetate with 1-aryl-2-haloalkan-1-ones has been investigated. It has been found that, depending on the nature of the halogen atom in 1-aryl-2-haloalkan-1-ones and the reaction conditions, alkylation or olefination products can be obtained with excellent or even full selectivity.

alkylations - Horner-Wadsworth-Emmons olefination - regioselectivity - ethyl diethoxyphosphorylacetate - α-haloketones

References

1a Taylor EC. Davies HML. J. Org. Chem.  1986,  51:  1537 

1b Dowd P. Wilk BK. Synth. Commun.  1993,  23:  2307 

1c Gallager PT. Hicks TA. Lightfoot AP. Owton WM. Tetrahedron Lett.  1994,  35:  289 

1d Yamazaki S. Takada T. Imanishi T. Moriguchi Y. Yamabe S. J. Org. Chem.  1998,  63:  5919 

2a McDonald IA. Lacoste JM. Bey P. Wagner J. Zrieka M. Palfreyman MG. J. Am. Chem. Soc.  1984,  106:  3354 

2b Gebler JC. Woodside AB. Poulter CD. J. Am. Chem. Soc.  1992,  114:  7354 

2c Eguchi T. Aoyama T. Kakinuma K. Tetrahedron Lett.  1992,  33:  5545 

3 Klopsch R. Schlüter A.-D. Tetrahedron  1995,  51:  10491 

4a Sakai T. Amano E. Miyata K. Bull. Chem. Soc. Jpn.  1987,  60:  1945 

4b Bonadies F. Cardilli A. Lattanazi A. Orelli LR. Scettri A. Tetrahedron Lett.  1994,  35:  3386 

5 Fujiwara K. Nippon Kagaku Zasshi  1963,  84:  656 ; Chem. Abstr. 1964, 60, 524

6 Fox DJ. Pedersen DS. Warren S. Org. Biomol. Chem.  2006,  4:  3102 

7 Touil S. Zantour H. Phosphorus, Sulfur Silicon Relat. Elem.  1997,  131:  183 

8a Baszczyk E. Krawczyk H. Janecki T. Synlett  2004,  2685 

8b Janecki T. Baszczyk E. Studzian K. Janecka A. Krajewska U. Różalski M. J. Med. Chem.  2005,  48:  3516 

8c Albrech A. Kūdzia J. Koszuk JF. Warzycha E. Janecki T. Tetrahedron Lett.  2006,  47:  2353 

9 Ogata M. Matsumoto H. Kida S. Shimizu S. Tawara K. Kawamura Y. J. Med. Chem.  1987,  30:  1497 

10 Matsumoto T. Ishida T. Takeda Y. Soh K. Kubo I. Sakamoto M. Chem. Pharm. Bull.  1995,  43:  216 

11

Values for specific isomer were taken from the spectrum of the mixture of isomers.