Catalytic asymmetric methallylation of ketones with an (H8-BINOLate)Ti-based catalyst

Org Lett. 2006 Sep 28;8(20):4413-6. doi: 10.1021/ol061417y.

Abstract

The first catalytic asymmetric methallylation of ketones is reported. The catalyst, which is generated from titanium tetraisopropoxide, H8-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 beta-hydroxy ketones, which are not readily prepared from direct asymmetric aldol reaction of acetone with ketones.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Catalysis
  • Ketones / chemistry*
  • Titanium / chemistry*

Substances

  • Ketones
  • Titanium