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 journalArticle

13 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

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Methylation
Alkylation
Lithium
Amides
Esters

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Double stereocontrol in α-alkylation of chiral lithium dienolates generated from (E)-α,β-olefinic amides and esters. / Tomooka, Katsuhiko; Nagasawa, Atsushi; Nakai, Takeshi.

In: Chemistry Letters, No. 10, 01.01.1998, p. 1049-1050.

Research output: Contribution to journalArticle

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