You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via23.14.1.2.7.1 Variation 1: Polycyclic Ketones by Intramolecular [2+2] Cycloaddition of Monoalkylketenes with Alkenyl Groups
Please login to access the full content or check if you have access via
Tidwell, T. T., Science of Synthesis, (2006) 23, 606.
The intramolecular cyclization of ketenes with C=C bonds is a powerful technique for the construction of polycyclic rings, and is the subject of several reviews.[142–144] In the absence of other reagents to react with the ketene by intermolecular reactions, cyclization processes are favored, and some very strained rings can be obtained by this process. The conformational constraints on the reaction usually result in a high degree of stereoselectivity. Monoalkylketenes are not highly reactive, and so these cyclizations are most successful with highly nucleophilic alkenyl groups or when the reactive groups are held close together in cyclic structures.
Meeeeeeeeeeeee 888 (M8 = M, Me, Me), eeeeeeee ee eeeeeeeeeeeeeeeeeee ee eee eeee eeeeeeeee 888, eeeeeee eeeeeeeeeeeeee [8+8] eeeeeeeeeeeee ee eeee eee eeeeeeee eeeeeee 888 ee 8, 88, eee 88% eeeeee, eeeeeeeeeeee[888,888] (Meeeee 88). Mee eeee eeeeee eeeee eeee eee eeeeee- eee eeeeee-eeeeeeeeeee eeeeeee eeeeee eeeeeeee eee eeeee eeeeeeeee ee eee eeeeeeeeee eeeee, eeee eeeeeeee eeeeee eeeeeee ee eee eeeeeeeeeee eeeeee. Mee eeee ee eee eeeeeee eeee ee eeeeeeeee, ee eeeeeeeeee ee 888 (M8 = Me) ee eeeeeeeeeeeee Meeee eeeeeeeeeeeee eeeee eee eeeeeeeeeeeee 888 ee 88% eeeee,[888] eeeeeee eeeee eee eeee eeeeeeeeee, eeeeeeeeeee ee (8-eeeeeeeee-8-eeee)eeeeee (888), eeeeeeee eeee eee eeeee eeeeee 888, ee eeee eee eeeeeee[8.8.8] eeee eeeeee 888 ee eeee eeee eeeeeeeee, eee e eeeeeeee eeeee ee eeeeeeee eeeeeee (Meeeee 88).[888]
Meeeee 88 Meeeeee[8.8.8]eeeeee-8-eee Meeeeeeee ee Meeeeeeeeeeeee [8+8] Meeeeeeeeee ee Meeeeeeeeeeeeeeeee[888]
Meeeeee eeeeeeeee ee eeeeeeeeeeeee Meeee eeeeeeeeeeeeee eeeee eeeeeeeeeeeeeeee eeee eeeeeee eeeeeeeeeeeeee ee eeee eeeeeeeeeeeeee; eee eeeeeee, eee [(eeeeeeeeeeeeeee)eeeee]eeeeee 888, eeeeeeeee eeee eee eeeeeeeeeee 888, eeeeeeee ee eeee eee eeeeeeeee eeeeeeee 888 (Meeeee 88).[888] Meee eeeeeeee eeee eee eeeee eeee eee eeeeee 888 ee eeeeeeeee ee eeeeeeeeeeeeeeeeeee ee eee eeee eeeeeeee ee ee eee eeeeeee ee eeeeeee, eee ee eeeeeeee ee ee ee eeeeeee-eeeee eeeeeeee.[888]
Meeeee 88 Meeeeeeee Meeeeeee Meeeeeeee ee Meeeeeeeeeeeee [8+8] Meeeeeeeeee ee e Meeeeeeeeeeeeee Meeeeeeee ee Meeee Meeeeeeeeeeee[888]
Meeeeeeeee ee eee eeeee eeeeee 888 eeeee eee (eeeeeeeeeeeeeeeeeee)eeeeee 888, eeeee eeeeeeee ee eeee eee eeeeee eeeeeeee eeeeeeeee eeeeee 888 ee eeeeeeeeeeeeee [8+8] eeeeeeeeeeeee (Meeeee 88).[888]
Meeeee 88 Meeeeeeee Meeeee Meeeeeeee ee [8+8] Meeeeeeeeeeee ee e Meeeee[888]
Meeeeeeeeeeeeeeeeee ee eeee eeeeeeee 888 eeee eeeeeeeeeeeee eeeee eee eeeeeeee eeeeee 888, eeeee eeeeeeeee eeeeeeeeeeeeee [8+8] eeeeeeeeeeeee ee eeee eee eeeeeeeeeee eeeeee 888 (Meeeee 88).[888]
Meeeee 88 Meeeeeee Meeeee Meeeeeeee eee eee Meeeeeeeeeeeee [8+8] Meeeeeeeeee[888]
Meeee eeeeeeee eeeeeee eee eeeeeeeeeee ee eeeeee 888, eeeeeeeee eeee eeeeeee eeee 888 eeee 8-eeeeee-8-eeeeeeeeeeeeeeee eeeeee (Meeeeeeee'e eeeeeee; 88), ee eeee eee eeeeeeeeeee eeeeee 888;[88] eee eeeeeeeee ee eee eeeeeeeeeee eeeeee 888 eeee eeeeee 888 eeeeeeeee ee Meeee eeeeeeeeeeeee ee eeeee eeeeee 888;[888] eee eee eeeeeeeeee ee eeeeee 888 eeee eeee eeeeeeee 888 eeee eee eeeeee 888 (Meeeee 88).[888]
Meeeee 88 Meeeeeeeee Meeeeee ee Meeeeeeeeeeeee [8+8] Meeeeeeeeeeee ee Meeeeeeeeeeeeeee eeee Meeeeee[88,888,888]
Meeeeeeeeeee Meeeeeeee
Meeeeeeeee[8.8.8.88,8.88,8]eeeee-8-eee (888); Meeeeee Meeeeeeee:[888]
M eeee ee eeee eeeeeeee 888 (8.8 e, 88.8 eeee) ee eeeeeee (888 eM) (MMMMMMM: eeeeeeeeee) eee eeeee eeee 88 eee ee e eeeeeee, eeeeeeeee eeeeeee ee Me8M (8.88 e, 88 eeee) ee eeeeeee (888 eM). Mee eeeeeee eee eeeeeeee eee 8 e, eeeeee, eeeeee M8M (8 ×), eee eeeee. Mee eeeeeee eee eeeeeee ee eeeeeeeeeeee ee eeeeeeeeeee eeeeeeee. Meeeeeeeeeeeee (eeeeee eee, eeeeeee) eeeeeeee ee eeeeeeeeeee eeee eeeee eeeeee; eeeee: 8.8 e (88%); ee 888–888.8°M (MM).
References
| [52] | Meee, M. M.; Meeeeee, M. M.; Meeeeeee, M. M., Meeeeee, (8888), 88. |
| [142] | Meeeee, M. M., Meee. Mee., (8888) 88, 888. |
| [143] | Meeeee, M. M., Meeeeeeeee: Mee. Meee., (8888) 8, 888. |
| [144] | Meeeee, M. M., Mee. Meeeee Mee. Meee., (8888) 8, 88. |
| [145] | Meeeeee, M. M.; Meee, M. M., Me., M. Meee. Mee., Meee. Meeeee., (8888), 8888. |
| [146] | Meeeó, M.; Meeeeeee, M.; Meeeeee-Meeeeee, M.-M.; Meeee, M.; Meeeee, M.; Meeee, M.; Meeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [147] | Meeeee, M.; Meeeee, M.; Meeeeeee, M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [148] | Meeeeeee, M.; Meeeeeee, M., Meeeeeeeeee Meee., (8888), 8888. |
| [149] | Meeeee, M. M., Me.; Meee, M. M.; Meee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [150] | Meeee, M.; Meeeee, M. M., Meeeeeeeeee Meee., (8888), 8888. |
| [151] | Meeeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88-8, 8888.
Return to Top