S. V. Malhotra / Tetrahedron: Asymmetry 14 (2003) 645–647
647
Scheme 1.
ides. The highest recorded ee for the conversion of
cyclohexene oxide 1 to 2-cyclohexen-1-ol 2 using a
catalytic system has been achieved with lithium
DIPAM. These results certainly promise the catalytic
application of DIPAM and similar pinene-based lig-
ands in the complex synthesis of natural products and
biologically important compounds.
16. Sabol, J. S.; Cregge, R. J. Tetrahedron Lett. 1989, 30,
3377.
17. Asami, M.; Ishizaki, T.; Inoue, S. Tetrahedron: Asymme-
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Acknowledgements
21. Sodergren, M. J.; Andersson, P. G. J. Am. Chem. Soc.
1
998, 120, 10760.
An SBR grant (c 421120) from the NJIT for this work
2
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2. Seki, A.; Asami, M. Tetrahedron 2002, 58, 4655.
3. Gayet, A.; Bertilsson, S.; Andersson, P. G. Org. Lett.
is gratefully acknowledged.
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4. Brown, H. C.; Ramachandran, P. V. In Reductions in
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1
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drous MgSO . Column chromatography (silica, pentane/
4
Et O, 90/10) and removal of solvents gave the product
2
3
2-cyclohexen-1-ol (0.087 g, 89%). The spectroscopic prop-
erties of this product were identical to those reported in
1
28
the literature. The MTPA (Mosher) ester of the product
29
alcohol was prepared and analyzed using a gas chro-
matograph fitted with SPB-5 capillary column to estab-
lish the ee.
6
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