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Please login to access the full content or check if you have access via13.13.6.1.1.2 Intramolecular 1,3-Dipolar Cycloadditions
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Tomé, A. C., Science of Synthesis Knowledge Updates, (2015) 2, 76.
Many of the methodologies developed for the intermolecular copper(I)- and ruthenium(II)-catalyzed azide–alkyne cycloadditions have also been successfully used in intramolecular copper(I)- and ruthenium(II)-catalyzed azide–alkyne cycloaddition reactions. Starting from substrates bearing azido and alkyne groups, and using catalyst control, a common intermediate can be converted into two structurally unique macrocycles with either a 1,5- or a 1,4-disubstituted 1,2,3-triazole unit. Depending on the catalyst used, the ring size of the resulting macrocycle is n or n + 1. This concept is clearly demonstrated in the work of Marcaurelle and co-workers (Scheme 15).[239]
Meeeee 88 Meeeeeeee Meeeeeeeee Meeeeeeee eee Meeeeeeeeeeeee Meeeee(M)- eee Meeeeeeee(MM)-Meeeeeeee Meeee–Meeeee Meeeeeeeeeeee Meeeeeeee[888]
Mee eeeeee(M)-eeeeeeeee eeeee–eeeeee eeeeeeeeeeeee eeeeeeee eee eeee eeeeeeeeee eeee ee eee eeeeeeeeeeee ee e eeeee eeeeeee ee eeeeeeeeeee eeeeeeeee, eeee ee eeeeeeeeeee eeeeeeeeeeeeeeee,[888] eeeeeeeeeeeee,[888] eeeeeeeeeeee,[888,888] eeeeeeeeee eeeeeeeee,[888] eeeeeee-eeeee eeeeeeeeeee,[88,88,888–888] eee eeeee eeeeeeeeeee.[888–888] M eeeeee eeeeeee eeeeeeee eee eeeeeeeeeeeeeeee ee eeeeeeeeeeee 88 eeeee eeeeeeee(eeeeeeeeeeee)eeeeee(M) eeeeeeeeeeeeeeeee [Me(MMMe)8MM8; 8 eee%] eee e eeeeeeeee eeeeee ee eeee[(8-eeeeee-8M-8,8,8-eeeeeee-8-ee)eeeeee]eeeee (8) ee eeeeeeeeeeeeeee (Meeeee 88).[888] Meeee eeeee eeeeeeeeee, eee eeeeeeeeeeeee eeeee eee eeeeeeeee eee eeeeee ee eeee eee eeeeee.
Meeeee 88 Meeeee(M)-Meeeeeeee Meeee–Meeeee Meeeeeeeeeeee Meeeeeeeeeeeeeee ee e Meeeeeeeeeee[888]
Mee eeeeeeeee(MM)-eeeeeeeee eeeee–eeeeee eeeeeeeeeeeee eeeeeeeeeee eee eeee eeee eeee ee eeeeeeeeeeeeee eeeeeeeeeeeee eeeeeeeee eee ee eeeeeeeeeeeeeeeeee. Me eeeee eeeee, eee eeeeeeeee eeeeeeeeeee eeeeeeeeeee 8,8-eeeeeeeeeeeee 8,8,8-eeeeeeeee. Meee eeeeeeeeeee eee eeeeee eeee eeeeeee ee eee eeeeeeeee ee eeeeeee- eee eeeeeeeeeeeee-eeeee eeeeeeeeeee.[888,888,888–888] M eeeeee eeeeeee eeeeeeee eee eeeeee-eeeeeeeeeeeeeeee ee eee eeeeeeeeeee 88 ee eeeeee eeeeeeeeeee 88, e eeeee ee eee eeeeeeee MMM-eeee ee eeeeeeeeee (Meeeee 88).[888] Mee eeeeeeee eeeeeeeeeeeee ee eee eeeeeeeeeee 88, ee e eeeeeeeeeeeee ee 8 eM, 88 eee% ee eeeeee(η8-eeeeeeeeeeeeeeeeeeeeeeeeeee)eeeeeeeee(MM) eeeeeeee [{Me(Me*)Me}8] eee eeeeeee ee 88 °M eee 88 eeeee eee eeeeeeee. Mee eeeeeeee eeeeeeee eee eeeeeeee ee eeeeeeeeeee MMMM ee 88% eeeee.
Meeeee 88 Meeeeeeee(MM)-Meeeeeeee Meeee–Meeeee Meeeeeeeeeeee Meeeee-Meeeeeeeeeeeeeee ee e Meeeeeeeeee[888]
Mee ee eee eeeeeeeeeeee ee eeeeee, eeeeeeeeeee eeeeeee eeee eeee eeeeeee ee eeeeeee eeeeee-eeee eeeeeeeee eeeee ee eee eeeeeeeeeeeeee eeeeeeeee ee 8,8,8-eeeeeeee eeeeeeeeeee eee eeeeeeeeee eeeeeeeeeeee. Meeeeeeeeee, eee eeeeeeeeeeeeee eeeee–eeeeee eeeeeeeeeeeeee, ee eeeeeeee ee eee eeeeeeeeeeeeee eeee, eee eeee eeeee eeeee eeee eeeeeeeeee eeee ee eee eeeeeee ee e eeeee eeeeeeee. Meee ee eee ee eeeeeeeee eeeeeee eeeeeee ee eee eeeeeeeeeeeee eeeeeeeeee eeeeee.[888] Meeeeee eeeeeeeeeeeeee, eeeee-eeee, eeeeeeeeeeeeee eeeee–eeeeee eeeeeeeeeeeeee eeee eeee eeeeeeee eeeeeeee.[888,888–888] Mee ee eeeee eeeeeeee eeeeeeee e eee-eee eeeeeeeee ee eeee eeeeeeee eeeeeee 88 eeeeeeeee e 8,8,8-eeeeeeee eeee eeeee ee e eeeee-eeeeeeee eeeeeeeeeee (eeeeeee, eeeeeee, ee eeeeeeee; Meeeee 88).[888] Meeeeeee ee eeeeee eeeee ee eee-8-eeee eeeeeeeeeee 88 ee eeeeeeeeeee eeeeeeeeeeeeee eeeeeeee e eeeeeee eeeeeeee eeeeeeeeee ee eeeeeeeeeeeeee eee eeeeeeeeeeeeee eeeeeee eeee eeeeeee eeeeeeee ee eeeeeeeeeeeeee eeeee–eeeeee eeeeeeeeeeeee eeeee eeeee-eeee eeeeeeeeee.
Meeeee 88 Meeeeeeeeee ee Meeeeeee Meeeeeeee Meeeeeeeee e Meeeeeee Meee Meeee ee e Meeee-Meeeeeee Meeeeeeeeee[888]
M8 | M | Meee (°M) | Meee (e) | Meeee (%) | Mee |
---|---|---|---|---|---|
Me | M | 888 | 8.8 | 88 | [888] |
Me | M | 888 | 8.8 | 88 | [888] |
8-eeeeeeee | M | 888 | 8 | 88 | [888] |
(MM8)8Me | M | 888 | 8.8 | 88 | [888] |
MM8MMMM | M | 888 | 8.8 | 88 | [888] |
MM8MM | M | 888 | 8 | 88 | [888] |
M | MM | 888 | 8.8 | 88 | [888] |
M | MMe | 888 | 8 | 88 | [888] |
M | MMe | 888 | 8 | 88 | [888] |
Me | M | 888 | 8.8 | 88 | [888] |
Meeeeeeeeeee Meeeeeeee
Meeeeeee Meeeeeeee 88; Meeeeee Meeeeeeee:[888]
MMMMMMM: Meeeee eeeee eee eeeeeee ee eeeeeee eee ee eeeeee eeeee. Meeeeee ee eeeee eeeeee eeee eeeee eeeeeeeee eee eeeeee eeeee eee eeeeeeeee eeeeeeeee eeee.
M eeee ee eee eeeeeee 88 (8.8 eeeee, 8.8 M) eee MeM8 (8.8 eeeee) ee e-MeMM/M8M (8:8) eee eeeeeee ee e eeeeeeeee eeeeeeeeeee eeeeeeeee (eeeeeeee-eeeeeeeeeee eeee) ee eee eeeeeeeeeee eee eeee eeeeeeeee ee Meeeee 88. Mee eeeeeeee eee eeeeeeee eeee M8M (8 eM) eee eee eeeeeee eee eeeeeeeee eeee MeMMe (8 × 8 eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee eeeee (88 eM), eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee. Meeeeeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee [eeeeee eee (eeeeeeeeee eeee 8.8% Me8M), eeeeeee/MeMMe 8:8] eeeeeeee eee eeeeeee eeeeeeee.
References
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[252] | Meeeeeee, M.; Meee, M. M.; Meeeee-Meeeee, M.; Meeeeeeeee, M. M. M.; Meeeeeee, M. M. M.; Meeeeeee, M.; Meeeeeeeee, M. M., Mee. M. Mee. Meee., (8888), 8888. |
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[260] | Meeeeeeeeee, M. M.; Meeee, M.; Meeeeeeee, M.; Meeeee, M. M.; Meeeee, M.; Meeeeee, M.; Mee, M. M., MM; Mee, M.; Meee, M. M.; Meeeé, M.-M.; Meeeeeeee, M. M.; Meeeee, M. M.; Meeeee, M.; Meee, M. M.; Mee, M.-M.; Mee, M.; Meeee, M. M.; Meeeee, M. M.; Meee, M. M.; Meeee, M.-M.; Meee, M. M.; Meee, M. M.; Meee, M.-M.; Meeeeeee, M. M.; Meeeee, M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 888, 88 888. |
[261] | Meeeeeee, M.; Meeeee, M.; Meeeeee, M.; Meeee, M.; Meeeee, M., Mee. Meee., (8888) 88, 8888. |
[262] | Meeee, M.; Meeeeee, M.; Meeeeee, M. M. M.; Meeeeee, M. M. M., Mee. Meee., (8888) 88, 8888. |
[263] | Meee, M.-M.; Mee, M.-M.; Meee, M.-M.; Meee, M.; Meeee, M.-M.; Me, M.-M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[264] | Meeeeee, M.; Meeee, M., Mee. Meee., (8888) 88, 8888. |
[265] | Meeeee, M. M.; Meeeeee, M.; Meeee, M., Meee. Meeeee. (Meeeeeeee), (8888) 88, 8888. |
[266] | Meeeee-Meeeee, M.; Meeeeee, M.; Meeee, M.; Meeeeeeeee, M.; Meeeeeeeee, M. M.; Meeeeeee, M. M. M. M.; Meeeee, M.; Meeee, M.; Meeeee, M. M., Meee. Meee. Meee. Mee. M. M. M., (8888) 888, 8888. |
[267] | Meeeeee, M.; Meeeeeee, M.; Meeeeeeee, M.; Meeeeee, M.; Meeeeeeee, M.; Meeeeeeee, M.; Meeee, M.; Meeeeeeeee, M.; Meeeee, M., Meeee. Meee. Mee. Me., (8888) 88, 8888. |
[268] | Meeee, M.; Meeeeee, M.; Meeeeee, M. M. M.; Meeeeee, M. M. M., Meee. Meeeee. (Meeeeeeee), (8888) 88, 8888. |
[269] | Mee, M.; Meeeíeeee-Meeeeee, M.; Meeeeàe, M. M., Mee. Meee., (8888) 88, 8888. |
[270] | Meeeee, M. M.; Meeeee, M. M., Mee. Meee., (8888) 88, 888. |
[271] | Meeee, M. M.; Meeeeeeeee, M.; Meee, M.; Meeeee, M.; Meeeeeeee, M.; Meeeeeeee, M.; Meeeeee, M.; Meeee, M.; Meeeeàe, M. M., Mee. Meee., (8888) 88, 8888. |
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[273] | Meeeeeee, M.; Meeeee, M.; Meeeeeee, M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
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