C -Alkylation of Functionally Substituted Carbanions with Cyclopropiminium Ions: A New Route to Cyclopropane Amino Acids

Ansgar Mertin, Thies Thiemann, Ian Hanss, Armin De Meijere

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

1-Diallylamino- and 1-dibenzylamino-1-cyclopropanols (3a,b) can easily be prepared in high yield from the corresponding secondary amines and cyclopropanone hemiacetal 1 (1-ethoxy-1-cyclopropanol). Their reactions with functionalized carbon nucleophiles such as ketene silyl acetals (1-methoxy-1-trimethylsiloxyethylene and methyl 3-methoxy-3-trimethylsiloxy-2-propenoate) and lithium enolates of alkyl esters under titanium(IV) chloride catalysis yield protected cyclopropane amino esters [1-aminocyclopropaneacetic acid derivatives]; subsequent deprotection to the free amino acids is also exemplified.

Original languageEnglish
Pages (from-to)87-89
Number of pages3
JournalSynlett
Volume1991
Issue number2
DOIs
Publication statusPublished - Feb 1991
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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