Generation and asymmetric Michael addition reaction of chirally N- protected α-aminoalkyl cyanocuprates

Takahiro Tomoyasu, Katsuhiko Tomooka, Takeshi Nakai

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Enantio-enriched α-aminopropylcyanocuprates, generated from the chirally N-protected α-aminopropylstannane (racemic at the Sn-bearing stereocenter) via Pearson's Sn/Li transmetalation protocol followed by treatment with copper cyanide, is shown to undergo an addition reaction to α,β-unsaturated aldehydes and ketones to give the γ-amino carbonyl compounds in higher stereoselective fashion. Of special interest is the reaction with acrolein and 2-cyclohexenone which affords the adducts as a single stereoisomer.

Original languageEnglish
Pages (from-to)345-349
Number of pages5
JournalTetrahedron Letters
Volume41
Issue number3
DOIs
Publication statusPublished - Jan 15 2000
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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