4
Tetrahedron
carbinolic center. Considering structurally related 1,2-
Appl. Chem. 2013, 85, 1683. (c) Witczak, Z. J., Chhabra, R., Chen, H.,
Xie, X-Q. Carbohydr. Res. 1997, 301, 167-175. (d) Witczak, Z. J.,
Mielguj, R. Synlett. 1996, 108-110. (e) Witczak, Z. J. Pure and Appl.
Chem. 1994, 66, 2189-2192.
1
2
aminoalcohols previously reported in our group, it is
possible to determine that the 1,3-aminoalcohols are more
enantioselective in the ZnEt addition to benzaldehyde. One
salient feature is that for 1,2-aminoalcohols the best
selectivities are observed with tertiary amino groups,
meanwhile the most efficient 1,3-aminoalcohols are the ones
with primary amino group.
2
8
.
Braun, C. E., Cook, C. D.; Merrit, C.; Rosseau, J. E., “9-
nitroanthracene”. Organic Syntheses 1963, Coll. 4, 711.
Kakuta, H.; Koiso, Y.; Nagasawa, K.; Hashimoto, Y. Bioorg. Med.
Cham. Lett. 2003, 13, 83.
9.
1
1
0. Sarotti, A. M.; Spanevello, R. A.; Suárez, A. G. Tetrahedron 2009, 65,
502.
3
1. Fringuelli, F.; Tatichi, A. Dienes in the Diels-Alder Reaction. John
Wiley & Sons. Nueva York. 1990. Chapter 6.
In summary, this is the first report of the preparation of
,3-aminoalcohols with primary and tertiary amino groups
1
12. Zanardi, M. M.; Botta, M. C. and Suarez, A.G. Tetrahedron Letters
014, 55, 5832.
2
derived from levoglucosenone and their application in the
enantioselective diethylzinc addition to benzaldehyde. The
syntheses of the aminoalcohols were simple and effective,
allowing to obtain the desired compounds in two or three
steps from levoglucosenone. The different substitution of
amino groups present in this new family of aminoalcohols,
show the adequate functionalization for further transformation
into other chiral derivatives. The level of induction obtained,
in addition to the fact that the starting material is easily
obtained from biomass, makes this system an excellent model
to be exploited in other asymmetric reactions and a starting
point for the development of new chiral catalysts or
organocatalyst.
1
3. (a) Da, Ch.; Han, Z.; Ni, M.; Yang, F.; Liu, D.; Zhou, Y.;Wang, R.
Tetrahedron: Asymmetry 2003,14, 659; (b) Cimarelli, C.; Palmieri, G.;
Volpini, E. Tetrahedron: Asymmetry 2002, 13, 2417; (c) Lu, J.; Xu, X.;
Wang, S.; Wang, C.; Hu, Y.; Hu, H. J. Chem. Soc., Perkin Trans. 2002,
1, 2900.
1
1
4. Noyori, R., Asymmetric catalysis in organic synthesis. John Wiley &
Sons. New York, 1994; pp 264.
5. Roudeau, R.; Gomez Pardo, D.; Cossy, J. Tetrahedron 2006, 62, 2388.
Acknowledgments
This research was supported by UNR, ANPCyT,
CONICET, Fundación J. Prats, Argentina, MMZ thanks
CONICET for the award of a fellowship.
Supplementary Material
Supplementary data (experimental procedures for the
1
synthesis of all compounds, characterization data, copies of H
1
and C NMR spectra of new products) associated with this
3
article can be found in the online version at….
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