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Organic Letters
Letter
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Figure 3. Probable catalytic cycle.
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In the present study, we have given a proof of concept that
chiral sulfinamide derivatives can be used as an efficient
organocatalyst in ARO of various meso-epoxides with anilines
to give corresponding enantioenriched β-amino alcohols (ee up
to >99%) with high yield (up to 95%). Based on the experimental
results with structural variation in the catalyst it was observed that
the chirality of sulfur determines the configuration of the
product.
27, 1677. (d) Carree
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, F.; Gil, R.; Collin, J. Tetrahedron Lett. 2004, 45,
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Zhao, J. C-G. Chem. Commun. 2013, 49, 9836. (h) Martin, M.; Hellani,
ASSOCIATED CONTENT
* Supporting Information
■
S
A. E.; Yang, J.; Collin, J.; Bezzenine-Lafollee
9801.
́
, S. J. Org. Chem. 2011, 76,
1H and 13C NMR spectra of products and reaction intermediates
and HPLC profiles of the products. This material is available free
(17) (a) Bartoli, G.; Bosco, M.; Carlone, A.; Locatelli, M.; Massaccesi,
M.; Melchiorre, P.; Sambri, L. Org. Lett. 2004, 6, 2173. (b) Kureshy, R. I.;
Prathap, K. J.; Kumar, M.; Bera, P. K.; Khan, N. H.; Abdi, S. H. R.; Bajaj,
H. C. Tetrahedron 2011, 67, 8300.
(18) Plancq, B.; Ollevier, T. Chem. Commun. 2012, 48, 3806.
(19) (a) Schneider, C.; Sreekanth, A. R.; Mai, E. Angew. Chem., Int. Ed.
2004, 43, 5691. (b) Mai, E.; Schneider, C. Chem.Eur. J. 2007, 13,
2729. (c) Azoulay, S.; Manabe, K.; Kobayashi, S. Org. Lett. 2005, 7, 4593.
(20) (a) Mai, E.; Schneider, C. Synlett 2007, 13, 2136. (b) Gao, B.;
Wen, Y.; Yang, Z.; Huang, X.; Liu, X.; Feng, X. Adv. Synth. Catal. 2008,
350, 385.
AUTHOR INFORMATION
Corresponding Author
■
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
(21) (a) Ogawa, C.; Azoulay, S.; Kobayashi, S. Heterocycles 2005, 66,
201. (b) Paster, I. M.; Yus, M. Curr. Org. Chem. 2005, 9, 1.
(22) Reddy, L. R.; Bhanumathi, N.; Rao, K. R. Chem. Commun. 2000,
2321.
CSMCRI Communication No. IMC-043-14. M.K. and R.I.K. are
thankful to CSIR-SRF, DST, and CSIR Network Project on
Catalysis CSC-0123 for financial assistance. M.K. is thankful to
AcSIR for Ph.D. registration. We are thankful to “Analytical
Science Discipline” CSIR-CSMCRI, G. B. Marg, Bhavnagar,
Gujarat, India, for instrument facilities and also Dr. B. Ganguly,
Principal Scientist, for DFT calculation from the same discipline.
(23) Pineschi, M. Eur. J. Org. Chem. 2006, 4979.
(24) (a) Tokuoka, E.; Kotani, S.; Matsunaga, H.; Ishizuka, T.;
Hashimoto, S.; Nakajima, M. Tetrahedron: Asymmetry 2005, 16, 2391.
(b) Chelucci, G.; Murineddub, G.; Pinnab, G. A. Tetrahedron:
Asymmetry 2004, 15, 1373. (c) Nakajima, M.; Saito, M.; Uemura, M.;
Hashimoto, S. Tetrahedron Lett. 2002, 43, 8827. (d) Malkov, A. V.;
Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.;
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