Double stereocontrol in α-alkylation of chiral lithium dienolates generated from (E)-α,β-olefinic amides and esters

Katsuhiko Tomooka, Atsushi Nagasawa, Takeshi Nakai

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

The methylation of the lithium dienolate generated from (E)-α,β-olefinic amide with Katsuki's chiral auxiliary affords the α-methylated β,γ-enamide in an exceptionally high Z-selectivity (99%) over the terminal olefinic bond along with 99% de at the α-chiral center. The origin of the high Z-selectivity is discussed.

Original languageEnglish
Pages (from-to)1049-1050
Number of pages2
JournalChemistry Letters
Issue number10
DOIs
Publication statusPublished - Jan 1 1998
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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