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0342981543
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For recent examples on sulfonyl imino dienophiles in ADAR, see for instance: (a) Bauer, T.; Szymański, S.; Jeźewski, A.; Gluziñski, P.; Jurczak, J. Tetrahedron: Asymmetry, 1997, 8, 2619.
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0346465004
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note
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See Supporting Information for detailed X-ray data.
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18
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0347725837
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note
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2, rt), giving rise to the dihydropyridine 5a in 55% ee from (R)-1a and 73% ee from (R)-1f (67-68% chemical yield).
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19
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0043261990
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For recent examples of α,β-unsaturated imino dienophiles in ADAR, see: (a) Loncaric, C.; Manabe, K.; Kobayashi, S. Adv. Synth. Catal. 2003, 345, 475.
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0346465002
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John Wiley & Sons: New York
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For instance, the tosylamides 5a and 5g, having an aryl and an alkenyl group at C-2 respectively, afforded the chiral 4-oxopiperidines 8a and 8g in satisfactory yields (58-64%, unoptimized) upon treatment with Zn/ AcOH at room temperature. For the deprotection of sulfonamides, see: (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed; John Wiley & Sons: New York, 1999; p 603-615. For the selective deprotection of p-nitrophenyl sulfonamides, see:
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Greene, T.W.1
Wuts, P.G.M.2
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(b) Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373.
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Jow, C.-K.2
Cheung, M.3
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23
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0347725836
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note
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2 provided enantiomerically pure compounds (>99.5% ee, 60-70% yield).
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