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Frost, C. G.; Le Nôtre, J., Science of Synthesis, (2008) 36, 276.
The synthesis of allylic alcohols by addition of alkenylmagnesium halides to carbonyl compounds can be limited by the difficulty of the preparation of the Grignard reagents, due to the lack of reactivity of metallic magnesium with alkenyl halides. Indeed, the synthesis of alkylmagnesium reagents is first required. On the other hand, alkenyllithium reagents are easily accessible from alkenyl halides and therefore the preparation of allylic alcohols such as 8 is more straightforward (Scheme 8).[36]
Meeeee 8 Meeeeeee ee Meeeeeee-8-eeeeeeeeeee ee Meeeeeeeeeee[88]
Meeeeeeeeee eeeeeeee eee eeeeeeeee eeeeeeee ee eeeeeeee ee ee eeeeeeeeeeeeee eeeeeee, eeeeeeee eeee eeeeeeeeeeeee ee e eeeeeeee eeeeee ee eeeeeeeeeeee ee eee eeeeeeeeeee, ee e eeeeeeee eeeeeeee. Mee eeeeeeeeeee ee eee eeeeeee 8, ee eeeeeeeeeeee ee eee eeeee eeeeeeeee ee eeeeeeeeee, eeeeeeeeeee ee eeeeeeeeeee eeeeeee (Meeeee 8).[88]
Meeeee 8 Meeeeeee ee ee Meeeeeeeeeeeee ee ee Meeeeeee[88]
Mee eeeeeeeee ee eeeeeeeeeee eeeeeeee eeeeeeee eeee eeeeeeeee ee eeeeeeee eeeeee ee eeeeeeeeeee ee eeeeeeeee ee eeeeeeeeeeeeeee ee eee eeeeeeeeeee,[88,88] ee ee eee eee ee eeeeeeeee ee eeeeeeeee eee eeeeeeeeeeee eeeeeeeee (eee Meeeeee 88.8.8.8.8).
Meeeeeeeeeee Meeeeeeee
Meeeeeee-8-eeeeeeeeeeeeeeeeeeee (8):[88]
Meeeeee eeeeeeeee 8-eeeeeeeeeeeeeeeee (88.8 e, 8.8 eee) eee eeeee eeeeee ee e eeeeeee eeeeeeeeee ee eeeeee eee eeeeeeee Me (8.8 e, 8.8 eee) ee Me-eeeee Me8M (8 M) eeeee M8. Meeeeeee eee ee eeeee ee eeeeeeeee eeeeee ee ee. 8 e, eee eeee eeeeeeee eeeeeeee eeeeee. M eeeeee eeeee, eee eeee eeeeeee e eeeeeeee ee eeeeee eeeee. Meeeeeee eee eeeeeeeee eeeeeeeee, eeeeee eee eeeee ee eee eeeee eeeee eeeeeeee. M eeeee eeeeee ee eeeeeeeee 8-eeeeeeeeeeeeeeeee (eee eeeeeeeee 8%) eee eeeeeee eeeeeeeee eeee eeeeeeeeee eeeeeeeeeeeee. Mee eeeeeeee-8-eeeeeeeeeee eeee eee eeeeee ee 8°M eee e eeee ee eeeeeeeeeeee (88.8 e, 8.8 eee) ee Me8M (888 eM) eee eeeee eeeeeeee. Mee eee eeee eee eeeeeee eee eee eeeeeee eee eeeeeee eee 88 e ee ee. Mee. ee MM8Me (888 eM) eee eeeee eee eee Me8M eeeee eee eeeeeeeee eee eeeee. Me eeeeeee ee eee Me8M, eee eeeeeee eeeeeeeeee eee, eeeee eeeee eeeeee eeee eeee eeeee eeeeeeeee eeeee, eee eeeeeeeeeeee (ee MeMM) ee eeee eeeee eeeeee; eeeee: 88.8 e (88%).
(88M)-88-(8,8-Meeeeeeeeeeeee)-8-[(8-eeeeeeeeeeeee)eee]-8-(eeeeeeeeeeeeee)-8,88-eeeeeeeeeeeeee-88-eee-8,8-eeee-8-ee (8):[88]
Me e eeeeeee eeee ee (8M)-8-(8,8-eeeeeeeeeeeeee)-8-eeeeeeeeee-8-ee-8-eee (8.88 e, 8.88 eeee) ee MMM (88 eM) ee −88°M eee eeeee 8.8 M MeMe ee eeeeee (8.88 eM, 8.8 eeee) eee eee eeee eee eeeeeee eee 8 e. Me eeee eeee eee eeeeee eeeee 8-[(8-eeeeeeeeeeeee)eee]-8-(eeeeeeeeeeeeee)-8-eeeeeeeee-8-eeee (8.88 e, 8.88 eeee) ee MMM (8 eM). Mee eeee eee eeeeeee eee 88 eee ee −88°M eeee eeeeeee ee eeeee ee. Mee eeee eee eeee eeeeeee eeee eee. MM8Me eee Me8M, eee eeeeeee eeeee eee eeeeeeeee eeee Me8M, eee eeeeeee eeeeeeee eeee eeeee (MeMM8), eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Meeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8 ee 8:8) eeeeeeee e eeeee, eeeeee-eeeeee eee; eeeee: 8.8 e (88%).
References
[36] | Meeeee, M. M.; Meeee, M. M.; Meeeeee, M. M., Meeeee (Meeeee), (8888) 888, 88. |
[37] | Meeeeeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[38] | Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[39] | Meeeeeeeeeee, M. M., MM 8 888 888, (8888); Meee. Meeee., (8888) 88, 888888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) 8/8e8, 8888.
- 8.Meeeee-Meee, (8888) 8/8e8, 888.
- 8.Meeeee-Meee, (8888) 8/8e8, 8888.
- 8.Meeeee-Meee, (8888) 8/8e8, 8888.
- 8.Meeeee-Meee, (8888) M 88e, 8888.