Short synthesis of skeletally and stereochemically diverse small molecules by coupling petasis condensation reactions to cyclization reactions

Naoya Kumagai, Giovanni Muncipinto, Stuart L. Schreiber

Research output: Contribution to journalArticlepeer-review

144 Citations (Scopus)

Abstract

(Chemical Equation Presented) An efficient synthetic pathway to skeletally and stereochemically diverse molecules is described. Densely functionalized amino alcohols were readily synthesized through a Petasis three-component, boronic acid Mannich reaction. Their intramolecular cyclization provided a collection of diverse single-isomer compounds with 15 different types of skeletons in three to five steps.

Original languageEnglish
Pages (from-to)3635-3638
Number of pages4
JournalAngewandte Chemie - International Edition
Volume45
Issue number22
DOIs
Publication statusPublished - 2006 May 26
Externally publishedYes

Keywords

  • Amino alcohols
  • Diversity-oriented synthesis
  • Multicomponent reactions
  • Petasis reaction
  • Synthesis design

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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