8
054
A. N. Thadani, R. A. Batey / Tetrahedron Letters 44 (2003) 8051–8055
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2
731–2737.
Scheme 3.
8
. (a) Batey, R. A.; Thadani, A. N.; Smil, D. V.; Lough, A.
J. Synthesis 2000, 990–998; (b) Batey, R. A.; Thadani, A.
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Batey, R. A.; Quach, T. D. Tetrahedron Lett. 2001, 42,
a- and b-substituted aldehydes utilizing potassium allyl
and crotyltrifluoroborates yields the corresponding
homoallylic alcohols in high yields and under very mild
conditions. The utility of this methodology was demon-
strated in a total synthesis of (−)-tetrahydrolipstatin,
which was accomplished in nine steps from dodecanal
with an overall yield of 35%. Further applications on
the use of trifluoroborate salts in organic synthesis are
currently underway in our laboratories and will be
reported in due course.
9099–9103; (d) Batey, R. A.; Thadani, A. N.; Smil, D. V.
Org. Lett. 1999, 1, 1683–1686; (e) Quach, T. D.; Batey,
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9
3830.
1
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Acknowledgements
1
The Natural Science and Engineering Research Council
50, 2000–2003.
(
NSERC) of Canada funded this research. R.A.B.
1
2. (a) Cornforth, J. W.; Cornforth, R. H.; Mathew, K. K. J.
Chem. Soc. 1959, 112–127; (b) Hoffman, R. W.; Weid-
mann, U.; Metternich, R.; Lanz, J. In Boron Chemistry;
Herm a` nek, S., Ed.; World Scientific Publishers: Singa-
pore, 1988; pp. 337–338; (c) Roush, W. R. In Houben-
Weyl, Stereoselective Synthesis; Helmchen, G.;
Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.;
Georg Thieme Verlag: Stuttgart, Germany, 1995; Vol.
E21b, pp. 1410–1486.
gratefully acknowledges receipt of a Premier’s Research
Excellence Award. A.N.T. thanks the NSERC of
Canada for postgraduate scholarships. We also thank
Dr. Alex Young for mass spectral analysis.
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