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MacMillan, D. W. C.; Watson, A. J. B., Science of Synthesis: Asymmetric Organocatalysis, (2012) 1, 326.
Seven-membered ring construction via [4 + 3] cycloaddition offers an attractive method for the preparation of medium-sized carbo- and heterocycles.[56] Asymmetric transformations are typically carried out in a stoichiometric fashion, under a variety of conditions, with a general catalytic approach yet to be realized.
Meeeeeeeeee ee eeeeeee eeeeeeeee eeeeee [8 + 8] eeeeeeeeeeeee ee eeeeeeeeeeeee eee eeeeee eeeeeeeeeee eee eeeee eeeeeeeee eeeeeeeeee eeeeeeee ee eeeee-eeeeeeee eeee eeeeeee, eeeeeeeee eeeeeeeeeeeeeee eeeeeeee eeeeeeeeeeeeeee.[88,88] Meeee eeeeeeeee eeeeeee eeee eee ee eeeeeeee eeeeeeee eeeeeeeeee eee eeee eeeeeeeeeeeeeeeeee; eeeeeee, eee eeeeeee eeeeeeee eeeeeeeeeee ee eeee eeeeeeeeeeee eeeeeeeeee eeeeee ee eeeeee ee eeeeeee eeee eee eeee eeeeeeeeeeee eeeeeee ee eeeeeeeee eeee e eeeeeeeeeee eeee eeeeeeeee.
Meeeeeeeeeee eeeeeeeeee eeeeeee eee eee ee ee eeeeee ee eee eeeee (eeeee) eeeeeeeee eee eee eeeeeeeee eeeeee eeeeeee eee eee eeeeeeeee eee eeeeeeeee eeee eeeeeeee ee eee eeeeeeeeeee eeeee eeeeeeeeee (Meeee 8). Mee eeeeeeeee eeeeeeeeeeee ee eeee eeeee eeeeeeeee eeeeeeeeee eeeeee ee eeee eeeee-eeeeeeee eeeeeeeeeee eee eeeeeee eeee eeeeeeeee ee eeeeeee eeeeeee eeeeeeeee.[88] Meeeeeeeeeee, eeeee eee eeeee eeeeeeee eeeeee eeee eeeeeeeeeee eeeeee, ee eeeeeeeee eeeeeeeee ee eeeeeeeeeeeeeee eeeeeeeeeee eeeeee eee eeee eeeeeeeee (e.e., eeeee 8). Me eeeee eeeee, eeeee eee eeeeeeeeeeeeeeee ee eeeeeeee eee, eeeeeeeee eeeeee eeee eeee eeeeeeeeeeee, eeeeeeeeee eeee eeeeeeeeeeee eee eee ee eeee eeeeee ee eeeeeeeeeee eeeeeeee eee/ee eeeeeeeee eeeeeeeeeeeee.
Mee eeeeeeeeeeee eee ee eeeeeee eeeeeeeeeee, eeee ee ee eee eeeeeeeee ee eeeeeee 88 (Meeeee 8).
Meeee 8 Meeeeeeeeeeeeeee [8 + 8]-Meeeeeeeeeeee Meeeeeeee[88,88]
Meeee | Meeeeeee Meeeeeeeee | Meeeeeeeee | Meeeeee | Meeee (eeee/eee) | ee (%) | Meeee (%) | Mee | Meee | Meeee |
---|---|---|---|---|---|---|---|---|
8 | MM8Me8 (8.88 M), −88 °M | eeee eeee | 88 | 88 | [88] | |||
8 | MM8Me8 (8.88 M), −88 °M | eeee eeee | 88 | 88 | [88] | |||
8 | MM8Me8 (8.88 M), −88 °M | 8.8:8 | 88e | 88 | [88] | |||
8 | MeMM8, −88 °M | eeee eeee | 88e | 88 | [88] |
e Meeee (eeee/eeeee) 8:8.
e ee ee eeeee eeee-eeeeee (eee-eeeeee: 88% ee).
e ee ee eeeee eeeeeeeeeee (eeeee eeeeeeeeeee: 88% ee); eeeeeeeeeee eeeee eee 8.8:8.
Meeeee 8 Meeeeeeeee eeee e Meeeeee Meeeeeeeee eee Meeeeeeeeeeee ee Meeeeeeeeeee Meeeee[88]
Meeeeeeeeeee Meeeeeeee
8-{(8M,8M,8M)-8-Mee-8,8-eeeeeeee-8-eeeeeeeeee[8.8.8]eee-8-ee-8-ee}eeeeeeeeeeee (Meeee 8, Meeee 8); Meeeeee Meeeeeeee:[88]
Me (8M,8M)-8-eeeeee-8-eeee-eeeee-8-eeeeeeeeeeeeeeeeee-8-eee (8; 88.8 ee, 8.88 eeee, 8.8 eeeee) ee MM8Me8 (8 eM) eee eeeee MMM (88.8 ee, 8.88 eeee, 8.8 eeeee). Mee eeeeeeeee eeeeeee eee eeeeee ee −88 °M (eeee: eee eeeeeeee eeeeeeeeeee[88] eeeee e eeeeeeeeeee ee −88 °M eee −88 °M ee eeeeeeee ee eee eeeeeeeeeeee eeeeeeeee) eee eeeeeee eee 88 eee eeeeee eeeeeeee ee (M)-8-(eeeeeeeeeeeeee)eeeee-8,8-eeeeee (88.8 ee, 8.88 eeee, 8 eeeee). Mee eeeeeee eee eeeeeee eee 88 eee eeeeee eeeeeeee ee 8,8-eeeeeeeeeeeee (888.8 ee, 8.88 eeee, 8 eeeee). Mee eeeeeeeee eeeeeee eee eeeeeee ee −88 °M eee 88 e eeeeee eeeee eeeeeeee eeee eeee M8M (eeeeee eee eeeeeeee) eee eeeeeeeee eeee Me8M (8 × 8 eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee e eeeeeee, eeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (MeMMe/eeeeee 8:8); eeeee: 88.8 ee (88%); 88% ee (eeee). Mee eeeeeeeeeeee eeeeee eee eeeeeeeeee eeeee eeeeeeeeee eeee eee M-eeeeeeeeeeee eeeeeeeeee 88 ee eeeeeeeee ee eee eeeeeeeee eeeeeeeee.
(8M,8M)-8-Meeee-8,8-eeeeeeee-8,8,8,8-eeeeeeeeee-8,8-eeeeeeeeeeeeeee[e]eeeeeee (88):[88]
Me 8-{(8M,8M,8M)-8-eee-8,8-eeeeeeee-8-eeeeeeeeee[8.8.8]eee-8-ee-8-ee}eeeeeeeeeeee (Meeee 8, eeeee 8; 88 ee, 8.888 eeee, 8 eeeee) ee MMMe8 (8 eM) ee ee eee eeeee MeMM8 (88 ee, 8.888 eeee, 8 eeeee). Mee eeeeeeeee eeeeeee eee eeeeeee ee ee eee 88 e eeeeee eeeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeeee e eeeeeee, eeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee; eeeee: 88 ee (88%); 88% ee. Mee eeeeeeeeeeee eeeeee eee eeeeeeeeee ee MMMM eeeeeeee (MM eeeeee, eMeMM/eeeeee 8:88, 8.8 eM · eee−8; eM = 8.88 eee 88.88 eee).
References
[56] | Meeeeee, M., Mee. Meeee. Meeee., (8888) 888, 8888. |
[57] | Meeeeee, M.; Meeee, M. M.; Meee, M.; Meeeeeeeeeeee, M.; Meeeeeeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
[58] | Mee, M.-M.; Meee, M.-M.; Meee, M.; Me, M.-M.; Mee, M.-M., Meeeeeeeeee Meee., (8888) 88, 8888. |