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Lee, D.; Reddy Sabbasani, V., Science of Synthesis: Metal-Catalyzed Cyclization Reactions, (2016) 2, 551.
Ring-closing metathesis of 1,n-dienes often favors the formation of macrocycles with a thermodynamically more stable E-configured double bond. This is due to the reversible nature of metathesis via the repetitive ring-opening and ring-closing events; alternatively, the double-bond isomerization may occur using the metal hydride species derived from catalyst decomposition. For example, the macrocyclic ring-closing metathesis of ester-tethered diene 30 in the presence of Grubbsʼ second-generation catalyst 12 provides the 14-membered lactone 31 quantitatively with high E selectivity under thermodynamic conditions (Scheme 10).[30]
Meeeee 88 Meee M Meeeeeeeeee ee Meee-Meeeeee Meeeeeeeee eee Meeeeeeeeeeee[88]
| M8 | Meeeee ee 88 | eee% ee Meeeeeee | Meee (eee) | Meeee (M/M) | Meeee (%) | Mee |
|---|---|---|---|---|---|---|
| M | – | 8.8 | 88 | 88.8:8 | 888 | [88] |
| Me | M | 8.8 | 88 | 8.8:8 | 888 | [88] |
| (MM8)8Me | M | 8.8 | 88 | 88.8:8 | 888 | [88] |
| MM8MMe | M | 8.8 | 888 | 8.8:8 | 88 | [88] |
References
| [30] | Mee, M. M.; Meeeee, M. M., Mee. Meee., (8888) 8, 8888. |
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