Catalytic asymmetric methallylation of ketones with an (H 8-BINOLate)Ti-based catalyst

Jeung Gon Kim, Elizabeth H. Camp, Patrick J. Walsh

Research output: Contribution to journalArticlepeer-review

38 Scopus citations

Abstract

The first catalytic asymmetric methallylation of ketones is reported. The catalyst, which is generated from titanium tetraisopropoxide, H 8-BINOL, 2-propanol, and tetramethallylstannane, reacts with ketones in acetonitrile to afford tertiary homoallylic alcohols in fair to excellent yields (55-99%) and fair to high enantioselectivities (46-90%). Ozonolysis of the resulting products provides access to chiral β-hydroxy ketones, which are not readily prepared from direct asymmetric aldol reaction of acetone with ketones.

Original languageEnglish (US)
Pages (from-to)4413-4416
Number of pages4
JournalOrganic letters
Volume8
Issue number20
DOIs
StatePublished - Sep 28 2006
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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