Quantum chemical calculations on the Peterson olefination with α-silyl ester enolates

…, JE Tønder, D Tanner, PO Norrby

Index: Gillies, Malcolm B.; Tonder, Janne E.; Tanner, David; Norrby, Per-Ola Journal of Organic Chemistry, 2002 , vol. 67, # 21 p. 7378 - 7388

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Citation Number: 17

Abstract

The reaction of stabilized Peterson reagents (α-silyl ester enolates) with ketones has been studied theoretically and experimentally. Enolate geometry was studied by trapping experiments and NMR spectroscopy and was found to differ markedly with the nature of the base (LiHMDS vs LDA vs KHMDS). The chelating effect of the lithium counterion was found to be critical for the reaction. For the two ketones studied, the combined weight of ...

~3%

Detail

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