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H3C
N
Zn
H
F3C
I
O
Scheme 7.
3. Conclusion
In conclusion, we have found three remarkable advantages
of the trifluoromethylated amino alcohol reduced in the
Simmons–Smith cyclopropanation of allylic amines; (1)
the trifluoromethylated amino alcohol auxiliary depressed
unwanted side reactions with its acidic hydroxy group;
(2) it accelerated the reaction rate remarkably, and (3) it
promoted excellent diastereoselectivity by the bulkiness of
its trifluoromethyl group. Easy introduction and removal
of this trifluoromethylated chiral auxiliary would be an
additional synthetic advantage. We are currently eager to
find further applications of the trifluoromethylated amino
alcohol ligands and auxiliaries for the stereoselective
reactions.19,20
4. Diastereoselective Simmons–Smith cyclopropanation with a
sugar auxiliary: (a) Charette, A. B.; Cote, B.; Marcoux, J.-F.
J. Am. Chem. Soc. 1991, 113, 8166–8167; (b) Charette, A. B.;
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Acknowledgments
We thank the SC-NMR Laboratory of Okayama Univer-
sity for 19F and H NMR analyses and the Venture Busi-
1
´
Charette, A. B.; Coˆte, B. J. Am. Chem. Soc. 1995, 117, 12721–
12732; (g) Kang, J.; Lim, G. J.; Yoon, S. K.; Kim, M. Y.
J. Org. Chem. 1995, 60, 564–577.
ness Laboratory of Graduate School of Okayama
University for the single-crystal X-ray diffraction analysis.
5. Diastereoselective Simmons–Smith cyclopropanation with a
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camphor auxiliary: Kaye, P. T.; Molema, W. E. Chem.
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