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A chiral 1,3,2-dioxaborolane derived from a natural diterpene for asymmetric reduction of prochiral ketones

Original Article

JOURNAL 1709

Organic Communications
VOLUME & ISSUE
Year: 2012 Issue: 2 April-June
PAGES
p.77 - 82
STATISTICS
Viewed 1515 times.
AUTHORS
    Diego A. Cifuente and Carlos E. Tonn
PDF OF ARTICLE

GRAPHICAL ABSTRACT

ABSTRACT

The application of a chiral 1,3,2-dioxaborolane, for the sulfide complex-mediated asymmetric reduction of prochiral ketones at room temperature, are described. The B-methoxy-dioxaborolane was synthesized from 2α,3α-dihydroxycativic acid, a labdane-type diterpene isolated from aerial parts of Baccharis scandens DC. Very good chemical yields (85-97%) and high enantioselectivities (62-96% ee), were obtained.

 KEYWORDS
  • Asymmetric reductions
  • chiral 1
  • 3
  • 2-dioxaborolane
  • 2α
  • 3α-dihydroxycativic acid.