✍ Scribed by M. Suzuki; A. Yanagisawa; R. Noyori
No coin nor oath required. For personal study only.
Reaction of a preformed lithium enolate and trimethyl orthoformate with added boron trifluoride leads to the corresponding o-dimethoxymethyl ketone. Formylation and related operations triggered by carbonyl functions are subjects perennially interesting to synthetic chemists. 1 One of the widely used methods stems on the in situ generation of enolates by exposure of ketonic substrates to strong bases such as sodium alkoxides or sodium hydride, followed by trapping by alkyl formates. However, this method, based on the high stability of the resulting 8-dicarbonyl compound enolates, is applicable only to primary alkyl ketones. Relevantly, reaction of ketones and orthoformamides affords the corresponding aminomethylene ketones. 2 Regiospecific cr-dialkoxymethylation is achievable by treatment of a mixture of an enol trimethylsilyl ether and an ortho ester by a stoichiometric amount of titanium
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## Site-specific ureidoalkylation of silyl enol ethers can be achieved by their Sumnary: reactions with chloromethylcarbamates at -78' under the influence of titanium tetrachloride.
## Abstract An α‐alkylation of the 2‐methylcycloalkanones 1 and 4 at the higher substituted carbon can be achieved by thioalkylation of the corresponding zinc enolates with the α‐chlorosulfides 3. The desulfurization can be carried out with either Raney nickel or lithium in diethylamine for compoun