Enantioselective synthesis of chiral allenoates by guanidine-catalyzed isomerization of 3-alkynoates

Hongjun Liu, Dasheng Leow, Kuo Wei Huang*, Choon Hong Tan

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

190 Scopus citations

Abstract

(Chemical Equation Presented) We report that chiral bicyclic guanidine 1 is found to catalyze the isomerization of alkynes to chiral allenes with high enantioselectivities. This Brønsted base catalyzed 1,3-proton shift reaction, an efficient and atom economical reaction, proceeds through deprotonation and protonation sequences. The axial chirality of the allenes is efficiently transferred to functionalized butenolides and cycloaddition products. We also successfully demonstrate the stereospecific synthesis of butenolide through allenoate cyclization with a catalytic cationic Au(I) complex.

Original languageEnglish (US)
Pages (from-to)7212-7213
Number of pages2
JournalJournal of the American Chemical Society
Volume131
Issue number21
DOIs
StatePublished - Jun 3 2009
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint

Dive into the research topics of 'Enantioselective synthesis of chiral allenoates by guanidine-catalyzed isomerization of 3-alkynoates'. Together they form a unique fingerprint.

Cite this