Highly diastereoselective construction of acyclic systems with two adjacent quaternary stereocenters by allylation of ketones

Takeshi Takeda, Masanori Yamamoto, Satoshi Yoshida, Akira Tsubouchi

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Unsymmetrical ketones and allyltitanocenes generated by the desulfurizative titanation of -disubstituted allyl phenyl sulfides react under highly diastereoselective construction of adjacent quaternary stereocenters (see scheme; R L=large group, R S=small group). The title reaction is stereospecific: the anti- and syn-homoallylic alcohols are obtained by the reaction of E- and Z-allylic sulfides, respectively.

Original languageEnglish
Pages (from-to)7263-7266
Number of pages4
JournalAngewandte Chemie - International Edition
Volume51
Issue number29
DOIs
Publication statusPublished - 2012 Jul 16
Externally publishedYes

Keywords

  • Allylation
  • Diastereoselectivity
  • Ketones
  • Synthetic methods
  • Titanium

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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