O-Silylation and Attempted O-Alkylation of Lithium Ester Enolates. The Synthesis of O-Silyl Ketene Acetals
- 1 January 1973
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 3 (1), 67-72
- https://doi.org/10.1080/00397917308062007
Abstract
The reaction of ketone enolates with alkylating or silylating reagents can be used to prepare O-alkyl or O-silyl vinyl ethers1. An analogous reaction of ester enolates would produce O-alkyl (I) or O-silyl (II) ketene acetals2. Such a simple route to ketene acetal structures would appear to be of major synthetic value3. Consequently, we have studied the reaction of lithium ester enolates, obtained from the corresponding esters and lithium N-isopropylcyclohexylamide (LiICA)4 as shown in eq. 1, with a variety of alkylating and silylating reagents.Keywords
This publication has 8 references indexed in Scilit:
- Protection of hydroxyl groups as tert-butyldimethylsilyl derivativesJournal of the American Chemical Society, 1972
- Claisen rearrangement of allyl estersJournal of the American Chemical Society, 1972
- Reaction of lithium N-isopropylcyclohexylamide with esters. Method for the formation and alkylation of ester enolatesJournal of the American Chemical Society, 1971
- Metal reductions of malonates and oxalates. A covenient decarboxylation route for disubstituted malonates and synthesis of keten acetalsJournal of the Chemical Society D: Chemical Communications, 1971
- Isolation of ketone enolates as trialkylsilyl ethersJournal of the American Chemical Society, 1968
- The synthesis and the rearrangement of O-silyl-O-alkyl keteneacetals into esters of silylacetic acidJournal of Organometallic Chemistry, 1966
- O-silyl-substituted enolsJournal of Organometallic Chemistry, 1964
- Silico-alkylation of Sodio Esters with Trimethyl-chlorosilane to Form Silyl Esters1Journal of the American Chemical Society, 1953