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2342524714
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We have reported highly enantioselective radical addition to vinylsulfones, in which a chiral Lewis acid selectively coordinates one of the enantiotopic sulfonyl oxygens and nitrogen in the heteroarylsulfonyl group: H. Sugimoto, S. Nakamura, Y. Watanabe, and T. Toru Tetrahedron: Asymmetry 14 2003 3045 3055
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8744317132
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The 2-pyridylsulfonyl group has been used for the synthesis of sulfonamides: H. Han, I. Bae, E.J. Yoo, J. Lee, Y. Do, and S. Chang Org. Lett. 6 2004 4109 4112
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40
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0035953314
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Recently, chiral 2-pyridinesulfonamide derivatives have been reported to have an inhibitory activity to the osteoclast-specific cysteine protease cathepsin K: R.W. Marquis, Y. Ru, S.M. LoCastro, J. Zeng, D.S. Yamashita, H.-J. Oh, K.F. Erhard, L.D. Davis, T.A. Tomaszek, D. Tew, K. Salyers, J. Proksch, K. Ward, B. Smith, M. Levy, M.D. Cummings, R.C. Haltiwanger, G. Trescher, B. Wang, M.E. Hemling, C.J. Quinn, H.-Y. Cheng, F. Lin, W.W. Smith, C.A. Janson, B. Zhao, M.S. McQueney, K. D'Alessio, C.-P. Lee, A. Marzulli, R.A. Dodds, S. Blake, S.-M. Hwang, I.E. James, C.J. Gress, B.R. Bradley, M.W. Lark, M. Gowen, and D.F. Veber J. Med. Chem. 44 2001 1380 1395
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more..
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42
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27944489875
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-
note
-
The reaction of 1a with a catalytic amount (0.3 equiv) of bis(oxazoline) 3 and MeMgBr gave 2a with 29% ee.
-
-
-
-
43
-
-
27944465220
-
-
note
-
2 afforded (S)-2a with 99% ee.
-
-
-
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45
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0029928097
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F.L. Merchan, P. Merino, I. Rojo, T. Tejero, and A. Dondoni Tetrahedron: Asymmetry 7 1996 667 670
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Merchan, F.L.1
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26844522419
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52
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0002829653
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Conversion to N-alkyl-N-sulfonyl compounds or N-Boc-N-sulfonyl compounds prior to the cleavage is needed for removal of a tosyl group from the primary amines, see: B. Nyasse, L. Grehn, and U. Ragnarsson Chem. Commun. 1997 1017 1018 and references cited therein
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Nyasse, B.1
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27944459973
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note
-
2 at room temperature. This amide was found to be 99% ee by HPLC analysis using CHIRALCEL OD-H.
-
-
-
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63
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0037415096
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For chiral relay in enantioselective reactions, see: O. Corminboeuf, L. Quaranta, P. Renaud, M. Liu, C.P. Jasperse, and M.P. Sibi Chem. Eur. J. 9 2003 28 35
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Sibi, M.P.6
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