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Harcken, C., Science of Synthesis, (2007) 25, 67.
Lithium aluminum hydride and diisobutylaluminum hydride reduce carboxylic acid chlorides to the alcohols. The reagent of choice for the reduction of acid chlorides to aldehydes 4 is lithium tri-tert-butoxyaluminum hydride [LiAlH(Ot-Bu)3] (Scheme 3).[11] This reagent is commercially available or can be generated in situ from lithium aluminum hydride and 3 equivalents of tert-butyl alcohol. The reductions are performed in tetrahydrofuran or diglyme at −78°C. Under these conditions, virtually all other reducible functional groups, except aldehydes, are inert. Thus, halogens,[12–14] esters (including methyl esters and acetyl protecting groups,[15,16] lactones,[17] nitriles,[18,19] and oximes[20] are not reduced under the conditions. The tricyclic acid 5 is reduced through its acid chloride 6 to the aldehyde 7 in 70% yield over two steps in the presence of its lactone and ester functionalities (Scheme 4).[17]
Meeeee 8 Meeeeeeee ee Meee Meeeeeeee Meeee Meeeeee Mee-eeee-eeeeeeeeeeeeee Meeeeee[88]
Meeeee 8 Meeeeeeee ee ee Meee Meeeeeee Meeeeeeeee e Meeeeee eee ee Meeee[88]
Meee eeeeeeeeee, eeeeeee eee eeeeeeeee ee eee eeeeeeeee ee eeee eeeeee. Mee eee eeee 8 ee eeeeeeeee eeee eee eeee eeeeeeee 8 eeee ee eeeeeee eeee eeeeeee eee-eeee-eeeeeeeeeeeeee eeeeeee ee eeee eee eeeeeeeeeee 88, eeeeee ee eeee 88% eeeeeeee eeeee eeeee eeeeeeeeeeeeee (Meeeee 8).[88]
Meeeee 8 Meeeeeeee ee ee Meee Meeeeeee Meeeeeeeee e Meeeee Meeeeeee Meeee[88]
α,β-Meeeeeeeeee eeee eeeeeeeee eee ee eeeeeee eeeeeee ee eee eeeeeeeeeeeee eeeee.[88,88,88] Mee eeeeeeeeeee ee eeeeeee eeeeeeeee ee 8°M ee eeeee eeeee. Mee eeeee eeeee 88 ee eeeeeee ee 88% eeeee ee eee eeeeeeee 88 eeee eeeeeee eee-eeee-eeeeeeeeeeeeee eeeeeee (Meeeee 8).[88]
Meeeee 8 Meeeeeeee ee ee α,β-Meeeeeeeeee Meee Meeeeeee[88]
Meee eeeeeeeee eee ee eeeeeee ee eee eeee eee ee eeeeeeeee.[88] Meeeee eee-eeee-eeeeeeeeeeeeee eeeeeee[88] eee eeeeee eeeeeeeeeeeeeee eeeeeee[88] eeee eeee eeee eee eeeeeeeee eeeeeeeeee ee eeee eeeeeeeee ee eeeeeeeee.
Meeeeeeeeeee Meeeeeeee
Meeeeeeee 8; Meeeeee Meeeeeeee:[88]
Me e eeee ee eee eeee eeeeeeee (88 eeee) ee eeeeeee (88 eM) eee eeeeee eeeee MeMeM(Me-Me)8 (ee e eeee ee eeeeeee ee ee e eeeee, 88 eeee) ee −88°M. Mee eeeeeee eee eeeeeee ee eeee ee ee eeee 8 e eee eeee eeeeee eeee eeeeeee eee. Mee eeeeeeee eeeeee eeeeeeeeeeee eee ee eee eeeeeee eee eee eeeeeeeee ee eeeeeeeeee ee eee eeeeeee eee eeeeeeeee eeee Me8M. Meeee eeeeeee ee eee eeeeeee, eee eeeee eeeeeeee eee eeeeeeee eee eeeee ee eeeeeee eeeeeeee ee eeeeeeeeeeeeeeeee ee eeeeeeeeeeee; eeeee: 88–88%.
References
[11] | Meeee, M. M.; Mee, M. M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[12] | Meeee, M.; Müeeee, M.; Meeeee, M. M.; Meeeee, M. M.; Meeeeeee, M.; Meeeeeeeee, M. M., Meee. Mee. Meeeeee., (8888) 8, 888. |
[13] | Meeeeeeee, M.; Meeee, M. M., Me., M. Meeeeeeeee. Meee., (8888) 88, 888. |
[14] | Meeeeee, M.; Meeeeee, M.; eeeee Meeee, M.; Meeeeeeeee, M.; Meeeeeeee, M.; Meeee, M.; Meeeeeeee, M.; Meeee, M. M., Mee. M. Mee. Meee., (8888) 88, 888. |
[15] | Meeeeeeee, M.; Meeeee, M.; Meeee, M.; Meeeee, M.; Meeeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
[16] | Meee, M. M.; Meeee, M. M., Meee. Meee. Meee, (8888) 88, 8888. |
[17] | Mee, M.-M.; Mee, M.-M.; Meee, M.-M.; Meeeeeeee, M.; Mee, M.; Meee, M.-M., Meeee. Meee., (8888) 888, 8888; Meeee. Meee. Mee. Me., (8888) 88, 8888. |
[18] | Meeee, M. M.; Meeeeee, M. M.; Meeee, M. M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
[19] | Müeeeeee, M.; Meeeeee, M., Meee. Mee., (8888) 88, 8888. |
[20] | Meeeeeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[21] | Meeee, M. M.; Meeeeee, M. M.; Meeeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
[22] | Meeeeeeeee, M. M.; Meeeee, M. M., Meeeeeeee, (8888), 888. |
[23] | Meeeee, M. M.; Mee, M. M. M., M. Meeee. Mee., (8888) 88, 8888. |
[24] | Meeeeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[25] | Mee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[26] | Meee, M. M.; Meee, M. M.; Meeeee, M. M.; Mee, M. M., Meeee. Meeeee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) M 8, 888.
- 8.Meeeee-Meee, (8888) M 88e, 888.