Page 95 - Catalysts for Fine Chemical Synthesis Vol 1 - Robert & Poignant

epoxidation of allylic alcohols 81

5.2.4 CONCLUSION

This method, specific for the epoxidation of allylic alcohols, gives good results
if the reaction is carried out under strictly anhydrous conditions, otherwise
the yield or the enantiomeric excess can decrease, sometimes dramatically.This
can explain the small differences between the results obtained during the
validation experiments and the published results. All the different reagents
are commercially available; they can be used as received but in case of low
yield and/or enantiomeric excess they should be distilled and dried under an
inert atmosphere. Table 5.1 gives some other examples of substrates which
can be epoxidized using the procedure described above.

5.3 ASYMMETRIC EPOXIDATION OF (E)-UNDEC-2-EN-1-OL USING
POLY(OCTAMETHYLENE TARTRATE)

D.C. Sherrington, J.K. Karjalainen and O.E.O. Hormi
Department of Pure and Applied Chemistry, Thomas Graham Building, University of
Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland, Tel: ‡44(0)1415482799,
m.p.a.smith@strath.ac.uk

5.3.1 SYNTHESIS OF BRANCHED POLY(OCTAMETHYLENE-l-(‡)-
TARTRATE) [5]

HO COO
COOH
H OH ∆ HO COO(CH 2 ) 8 x OOC COO(CH 2 ) 8 y
+ HO(CH 2 ) 8 OH
HO H O OH
(2)
COOH (CH 2 ) 8 OOC CO
(1)
HO OH
(3)

Materials and equipment
. l-(‡)-Tartaric acid, 10.0 g, 0.067 mol
. 1,8-Octanediol, 11.7 g, 0.080 mol
. p-Toluene sulfonic acid, 0.6 g
. Ethyl acetate
. n-Hexane

. 100 mL Three-necked round-bottomed flask with a magnetic stirrer bar; N 2
cylinderandbubbler; oilbath;hot-platestirrer;vacuumdistillationequipment