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Enantioselective carboxylation of a prochiral enolate in the presence of a chiral lithium amide

โœ Scribed by H Hogeveen; W.M.P.B Menge

Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
202 KB
Volume
27
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Ihe prochiral lithium 2,2,6-trimethylcyclohexenolate (2) was prepared from ketone 1 by deprotonation with lithium (S,S)-a,a'-dimethyldibenzylamide(4). Reaction of 2 with carbon dioxide at low temperature followed by methylation with metFy1 iodide yielded the corresponding ester 3 with an e.e. of 67%.

-Lithium amides (e.g. LDA, LiTMP) have established an important position in organic synthesis and are widely used as strong bases with low nucleophilicity. 1-3 Their chiral

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Enantioselective alkylation of lactams and lactones can be realized up to 98% ee by deprotonation with a chiral tetradentate lithium amide (4b) in the presence of lithium bromide, and subsequent alkylation with active alkylating agents in non-chelating solvents.

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