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Please login to access the full content or check if you have access via23.14.1.2.8 Method 8: β-Lactams by [2+2] Cycloaddition of Monoalkylketenes with Imines
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Tidwell, T. T., Science of Synthesis, (2006) 23, 608.
The [2+2] cycloaddition of ketenes with imines to form β-lactams (the Staudinger reaction) was discovered in 1907.[119] Because of the importance of the products in medicinal chemistry, this subject has been extensively examined, and previously published information regarding this product class can be found in Houben–Weyl, Vol. E 16b, pp 31–942, and in a number of reviews.[152–160] As with other ketene [2+2] cycloadditions, these reactions are often highly stereoselective (see Section 23.14.1.2.7), with a strong tendency to give a cis-stereochemistry of the substituents on the newly formed bond between the terminal carbon of the ketene and the carbon of the imine. However, imines have a higher tendency than alkenes to react by stepwise pathways to form zwitterionic intermediates, and so may show a lack of stereoselectivity in product formation.
Meeeeeeeeeee (8), eeee Meeee eeeeeeeeeeeee ee 8-eeeeeeeeeeee, eeeeeeeee [8+8] eeeeeeeeeeeee eeee eeeee 888 ee eeee β-eeeeee 888 (Meeeee 88).[888] Meeeeeeeeee eeeeeeeee ee eee eeee eee eeeeee eeee (eeeeeeeeeeeeeee)eeeeeee ee eeee eee eeeeeeeeeeeee β-eeeeee ee 88% eeeee.[888]
Meeeee 88 β-Meeeee Meeeeeeee eeee [8+8] Meeeeeeeeeeee ee Meeeeeeeeeee eeee ee Meeee[888]
Meeeeeeeee ee e eeeeeee-eeeeeee eeeee eeeeee 888 eeeee eee eeeeee 888, eeeee eeeeeeeee [8+8] eeeeeeeeeeeee eeee eeeeee (M)-M-eeeeeeeeeeeeeeeeeeee (888) ee eeee eee eeeee-β-eeeeee 888 (Meeeee 88).[888] Mee eeeeeee eee eeeeeeeee eee, eeee eeeeeeeeeee, eee eeeeee ee eee eeeeeeeeeee ee eeeeeeeeeeeeeee.[888]
Meeeee 88 Meeeeeeee ee e β-Meeeee ee [8+8] Meeeeeeeeeeee ee e Meeeeee-Meeeeee Meeeee eeee ee Meeee[888]
References
[119] | Meeeeeeeee, M., Meeeee Meeeeee Mee. Meee., (8888) 888, 88. |
[152] | Meeeeee, M. M.; Meeee, M. M., Mee. Meeee. (M. M.), (8888) 8, 888. |
[153] | Meeeee, M. M.; Meeee, M., 8,8-Meeeeeeeeeeee Meeeeeeee: Mee Meeeeeeee ee Meeee- eee Meee-Meeeeeee Meeeeeeeeeee, Meeeeeeeeeee: Mee Meee, (8888). |
[154] | eee eee Meeee, M. M.; eee Meeee, M., Meeeeeeeeee, (8888) 88, 8888. |
[155] | Meeee, M. M.; Meeeeeeee, M. M., Me Mee Meeeeee Meeeeeeee ee β-Meeeeee, Meeee, M. M., Me.; MMM: Mee Meee, (8888); ee 888–888. |
[156] | Meeeee, M.; Meeeeeee, M. M.; Meeeee, M.; Meeeeeee, M., Mee. M. Mee. Meee., (8888), 8888. |
[157] | Meeeee, M.; Meeeeeee, M. M.; Meeeee, M.; Meeeeeee, M., Meee. Mee. Meee., (8888) 88, 8888. |
[158] | Meeeee, M. M., Me Meeee Meee Meeeeeeeeeee, Meeeeee, M., Me.; Meeee: Mee Meee, (8888); Meee 8, Mee. 88, e 888. |
[159] | Me Meeee, M., Me Meeeeeeeeeeee Meeeeeeeeeee Meeeeeeee MM, Meeeeeeee, M. M.; Meee, M. M.; Meeeeee, M. M. M., Mee.; Meeeeeee: Meeeee, (8888); Mee. 8M, ee 888–888. |
[160] | Meeeee, M.; Meeeeeee, M. M.; Meeeee, M.; Meeeeeee, M., Meeeeee, (8888), 8888. |
[161] | Meeeee, M.; Meeeee, M., Meee. Mee., (8888) 88, 8888. |
[162] | Meeee, M. M.; Meee, M. M.; Meeeeee, M., Mee. M. Mee. Meee., (8888), 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8, 888.
- 8.Meeeee-Meee, (8888) M 88e, 888.
- 8.Meeeee-Meee, (8888) M 88e, 888.
- 8.Meeeee-Meee, (8888) M 88e, 888.