Page 12 - Volume 3, Issue 2, July 2010
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© Benaki Phytopathological Institute
Mihou & Michaelakis
42
2.2.Asymmetric syntheses via kinetic
resolution of racemic starting mate-
rials
2.2.1. Kinetic resolution of racemic 2-fury-
lundecanol
Kinetic resolution of racemic secondary
2-furylundecanol using catalytic amounts
of the titanium(IV)–tartrate complex was
achieved successfully, providing optically
active 2-furylundecanol (80–>98%
ee
) and
the corresponding optically active pyra-
none (Figure 13). Thus, utilizing (
S
)-1-(2-fur-
yl)undecanol as a chiral building block and
following functional and protective group
manipulations Honda furnished the desired
pheromone (Figure 14) (Kametani
et al.
,
1990)
(10 steps, 25% yield).
2.2.2. Kinetic resolution of allylic alcohols
Several approaches to (–)-(5
R
,6
S
)-6-ace-
toxy-5-hexadecanolide,
1a
, have exploited
the kinetic resolution of secondary or cyclic
allylic alcohols. In this regard, Mori and Otsu-
Figure 12
Figure 13
Figure 14
