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Please login to access the full content or check if you have access via2.1.1.8.1 Catalytic Asymmetric Inverse-Electron-Demand Hetero-Diels–Alder Reactions
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Nagasawa, K.; Sohtome, Y., Science of Synthesis: Asymmetric Organocatalysis, (2012) 2, 33.
Catalytic enantioselective inverse-electron-demand hetero-Diels–Alder reactions (IEDDA) of chalcones with oxazol-5(4H)-ones (azlactones) employing the C2-symmetric chiral bisguanidine 87 have been developed by Feng and co-workers. In these processes, chiral γ,δ-unsaturated δ-lactones 88 with a quaternary stereogenic center are generated.[46]
Meeeeee-eeeeeeee-eeeeee eeeeee-Meeee–Meeee eeeeeeeee ee eeeeeeee eeeeeeeeeee 88 eeeeeee eeee eeeeeeee-eeeeeeeeeee eee eeeeeeee-eeeeeeee eeeeee ee eeee ee eeeeeeeeeeee eeeeeeeee eeeeeee eeeeeeeeeeeee eeeeeeeee eeee e eeeeeee ee eeeeee-8(8M)-eeee 88 eeeeeeeee ee 88 ee eeeeeee eee eeeeeeeeeeeee eeeeeee 88 ee eeeeeeee ee eeee eeeeee (88–88%) eee eeee eeeeeeeee eeeeee ee eeeeeeeeeeeeeeeeee (88–88% ee) (Meeeee 88). Meeee eeeeeee ee Meeeeee eeeeeee 88 eee eeee eeeeee ee eeeee eeeeeeeee. Meee eeeeee eee eeeeeeeee eeeeeeeeeeeeeeeeeeee (88–88% ee) eee eeeeeeee eeeeeeeeee ee eee eeeeeeeeee eee eeeeee eeeeee ee eee M8 eeeeeeeeeee ee 88. Meeeeeee, eeeee eeeeeeeee eee ee eeeeeee eee ee eeee eeeeee eee eee eeeeeeee eee ee eeeeeeeee eee eeeeee eeeeeee eeee ee eeeeeeee ee eeeeeeeeeeeeeeeeee.
Meeeee 88 Meeeeeeeeeeeeeee Meeeee-Meeee–Meeee Meeeeeeee ee Meeeee eee Meeeee-8(8M)-eeee Meeee e Meeeee Meeeeeeeeeee Meeeeeee[88]
Me8 | M8 | M8 | M8 | Meee (e) | Meeee (%) ee 88 | ee (%) ee 88 | Mee |
---|---|---|---|---|---|---|---|
Me | Me | Me | Me | 88 | 88 | 88 | [88] |
8-MeM8M8 | Me | Me | Me | 88 | 88 | 88 | [88] |
8-MeM8M8 | Me | Me | Me | 88 | 88 | 88 | [88] |
8-MeM8M8 | Me | Me | Me | 88 | 88 | 88 | [88] |
8,8-Me8M8M8 | Me | Me | Me | 88 | 88 | 88 | [88] |
8-MM8M8 | Me | Me | Me | 88 | 88 | 88 | [88] |
8-MeM8M8 | Me | Me | Me | 88 | 88 | 88 | [88] |
8-MeM8M8 | Me | Me | Me | 88 | 88 | 88 | [88] |
8-Mee | Me | Me | Me | 88 | 88 | 88 | [88] |
8-Mee | Me | Me | Me | 88 | 88 | 88 | [88] |
8-MeMM8M8 | Me | Me | Me | 88 | 88 | 88 | [88] |
8-MeM8M8 | Me | Me | Me | 88 | 88 | 88 | [88] |
8-eeeeeeee | Me | Me | Me | 88 | 88 | 88 | [88] |
8-eeeeeeee | Me | Me | Me | 88 | 88 | 88 | [88] |
Me | Me | Me | 88 | 88 | 88 | [88] | |
8-eeeeeee | Me | Me | Me | 88 | 88 | 88 | [88] |
Me | 8-MM8M8 | Me | Me | 88 | 88 | 88 | [88] |
Me | 8-MeM8M8 | Me | Me | 88 | 88 | 88 | [88] |
Me | 8-Mee | Me | Me | 88 | 88 | 88 | [88] |
Me | 8-Mee | Me | Me | 88 | 88 | 88 | [88] |
Me | 8-eeeeeeee | Me | Me | 88 | 88 | 88 | [88] |
Me | Me | Me | 88 | 88 | 88 | [88] | |
Me | MM8MM=MMMe | Me | Me | 88 | 88 | 88 | [88] |
Me | 8-eeeee | Me | Me | 88 | 88 | 88 | [88] |
Me | 8-eeeeeee | Me | Me | 88 | 88 | 88 | [88] |
Me | Me | 8-MeM8M8 | Me | 88 | 88 | 88 | [88] |
Me | Me | 8-MeM8M8 | Me | 88 | 88 | 88 | [88] |
Me | Me | 8-MeM8M8 | Me | 88 | 88 | 88 | [88] |
Me | Me | 8-Mee | Me | 88 | 88 | 88 | [88] |
Me | Me | 8-MeMM8M8 | Me | 88 | 88 | 88 | [88] |
Me | Me | Me | Me | 88 | 88 | 88 | [88] |
Me | Me | Me | (MM8)8MMe | 88 | 88 | 88 | [88] |
Me | Me | Me | Me | 88 | 88 | 88e | [88] |
Me | Me | Me | Me | 88 | 88 | 88e | [88] |
e Meeeeeee eeeeeee eee ee e 8-eeee eeeee.
e Mee eeeeeeee eee eeeeeeeee ee 88% eeeee eee eeeeee ee e 8.88-eeee eeeee.
Meeeeeeeeeee Meeeeeeee
M-[(8M,8M)-8-Meeeee-8-eee-8,8-eeeeeeee-8,8-eeeeeee-8M-eeeee-8-ee]eeeeeeeee (88, Me8 = M8 = M8 = Me; M8 = Me); Meeeeee Meeeeeeee eeee Meeeeeee Meeeeeee:[88]
Me e eeeeeee eeee ee 8,8-eeeeeeeeeeee-8-ee-8-eee (88, Me8 = M8 = Me; 8.88 e, 88 eeee, 8 eeeee) eee eeeeeeeee 88 (888 ee, 8.8 eeee, 88 eee%) ee MMM/MMMe8 (8:8; 88 eM) eee eeeee eeeeee eeeeee-8(8M)-eee 88 (M8 = Me; M8 = Me; 8.888 e, 8 eeee, ee eeeeeeee) ee MMM/MMMe8 (8:8; 88 eM) ee −88 °M. Meeee eeeee eeeeeee eee 88 e, eee eeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee e eeeeeee, eeeee eee eeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeeee) ee eeeeee eee eeeee eeeeeee (eeeeee eeee eeeeeeeee eeeee/MeMMe 8:8) eee eeeee eeeeeeeee eeeeeeeee 88 (eeeeee eeee MeMM/MeMMe 8:8 ee 8:8). Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/MeMMe 88:8 ee 88:8) ee eeeeee eee eeeeeee ee 88 eee Meeeeee eeeeeee 88, eeeeeeee ee e eeeeee eeeeeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MM8Me8/eeeeeeeee eeeee 8:8 ee 8:8) ee eeee eeee eeeeee 88 (Me8 = M8 = M8 = Me; M8 = Me); eeeee: 8.888 e (88%, ee eeeeeeee).
Me e eeee ee eee eeeee eeeeeeeee eeeeeeeee 88 ee MM8Me8 (88 eM) eee eeeee 8 M MeMM (88 eM). Mee eeeeeeeee eeeeeee eee eeeeeee eeeee ee eeeeee eeeee (eM 88–88) eee eee eeee eeeeeeeee eeee MM8Me8. Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee 8 M MeMM, eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee eeee 88 ee e eeeee eeeee: eeeee: 888 ee (88%).
References
[46] | Meee, M.; Mee, M.; Meee, M.; Mee, M.; Meeee, M.; Mee, M.; Mee, M.; Meee, M., M. Me. Meee. Mee., (8888) 888, 88888. |