h+B=+C1GCWqÁpͧ ¦ Development and application of cage type amino alcohol organocatalyst v°_ 1Fv˺M 2FÎ]¼ 1FHK~c 1Fiª 3Fny¬q 4FJÉ^L 1 Ós¾{mÏ{ 1F\À{m 2F\mÏ£|m«6 3F\½m 4Ô h+B=+C1GCÕÊxÁpIÇPqU'¸)&[d &ÖJ!«s# ¹Í§', 2+ steric influence 3=CAC;E+B=+C1GC 1 1) Õ¯Q¨z% Ph Ph mh 2+3=CAC;EÑ)ÕÑ OH V-;BEÆP¸&®²_q)f* N H H non-covalent &Ö$ÕTÌÕ¯QXÆP»Ð enamine hydrogen formation site bonding site [²jÕ$²µdÆPÈj)& 2-azanorbornane $ÕWqÁpÒ¸)!' organocatalyst 1 & (Scheme 1)Ö$'Õh+B=+C1 Scheme 1 GC)WqÁp¦a kgSwÖ «Õh+B=+C1GCWqÁp¸)$ &)©¨ 2+3=CAC;EÁp 1 )¦&d[r¨¦I+C:G Ca )ÂÖ O µÕÁp 1 )¦&,2 O O catalyst 1 HO 7E 2 40D?/2=E 3 (20 mol%) + O # p<9D@E5+C8>: 4 O TFA (10 mol%) N N toluene H 40D?/2=E 3 ' H rt, 24 h 2 3 [2S, 3R]-5 'I+C:GCa Õ ºo[rb¢-;E7.Å OH O O catalyst 1 © ¨ & ¥ 5 (84%, (15 mol%) + 3 38% ee) # 6 (50%, 37% ee) H brine NO2 rt, 48 h NO2 $'ÕÁp 1 WqÁp [1R, 2R]-6 4 ¸)&$ Scheme 2 (Scheme 2)Ö Áp 1 #ÄuQ)¦'$a óÕ#I DielsAlder a 2,3) I¤[OZa &Áp¦!Rkg&Ö ×`¶¡Ø 1ÔH. Nakano, N. Kumagai, H. Matsuzaki, C. Kabuto, H. Hongo, Tetrahedron: Asymmetry, 1997, 8, 13911401. 2ÔH. L. Cui, F. Tanaka, Chem. Eur. J., 2013, 19, 62136216. 6216. 3ÔY. Kohari, Y. Okuyama, E. Kwon, T. Furuyama, N. Kobayashi, T. Otuki, J. Kumagai, C. Seki, K. Uwai, G. Dai, T. Iwasa, H. Nakano, J. Org. Chem., 2014, 79, 95009511. §¿·´N e v°_ Ó($ " x s¾{mrmrϤlY¥{r±t r} M1 «s d[r«s Ô
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