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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 30, 2000 - Issue 15
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Original Articles

Improved Cs2CO3 Promoted O-Alkylation of Acids

Jay P. Parrish Department of Chemistry, University of South Florida & Drug Discovery Program, H. Lee Moffitt Cancer Center & Research Institute, 4202 E. Fowler Avenue, Tampa, Florida, 33620-5250, USA
,
Eric E. Dueno Department of Chemistry, University of South Florida & Drug Discovery Program, H. Lee Moffitt Cancer Center & Research Institute, 4202 E. Fowler Avenue, Tampa, Florida, 33620-5250, USA
,
Seok-In Kim Department of Chemistry, University of South Florida & Drug Discovery Program, H. Lee Moffitt Cancer Center & Research Institute, 4202 E. Fowler Avenue, Tampa, Florida, 33620-5250, USA
&
Kyung Woon Jung Department of Chemistry, University of South Florida & Drug Discovery Program, H. Lee Moffitt Cancer Center & Research Institute, 4202 E. Fowler Avenue, Tampa, Florida, 33620-5250, USA
Pages 2687-2700 | Received 08 Oct 1999, Published online: 16 Feb 2011

References

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  • Dueno , E. E. , Chu , F. , Kim , S.-I. and Jung , K. W. 1999 . Tetrahedron Lett. , 40 : 1843 For our previous studies on cesium promoted alkylations, see
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  • Parrish , J. P. , Sundaresan , B. and Jung , K. W. 1999 . Synth. Commun. , in press
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  • Kunz , H. and Lerchen , H.-G. 1987 . Tetrahedron Lett. , 28 : 1873 For the pre-formation of cesium salts, see
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  • Sato , T. , Otera , J. and Nozaki , H. 1992 . J. Org. Chem. , 57 : 2166 For the in situ, conditions using CsF, see
  • Neither elimination nor trans-esterification was observed from the product mixtures. The only side product that was isolated was the diester (8%), derived from the double esterification of 1,2-dibromoethane (cf., entry 6, Scheme II)
  • Bonner , W. A. 1951 . J. Am. Chem. Soc. , 73 : 3126 Optical rotations of the produced products were compared with the reported values
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  • No side products such as the epimer at C(3) and elimination products were observed within our detection limits

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