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36.1.6.5.1 Variation 1: Addition of Organoaluminum Compounds

DOI: 10.1055/sos-SD-036-00173

Grosjean, C.; Whiting, A.Science of Synthesis, (200836263.

It is possible to access secondary and tertiary alcohols by the addition of triethylaluminum to esters (Scheme 14).[‌31‌] The secondary alcohol 33 is, however, the main product and it is likely that reduction follows the first addition of the ethyl group to the ester.

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Meeeee 88 Meeeeeee ee Meeeeeeeeeeeeeeee ee γ-Meeeee-δ-eeeeeeee eee γ-Meeeee-δ-eeeeeeee Meeeeee[‌88‌]

Meeeeeee ee eeeeeeeeeeeeeeeee ee eeee eeeeeeee eeeeeeee eeeee (e.e., 88 eee 88, Meeeee 88).[‌88‌,‌88‌]

Meeeee 88 Meeeeeee ee Meeeeeeeeeeeeeeee ee Meeeeeee[‌88‌,‌88‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeee-8-ee (88):[‌88‌]

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8-(eeee-Meeeeeeeeeeeeeeeeee)-8-eeeeeeeee-8-ee-8-eee 88; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meee eeeeeeeeeeeeeeeee ee eeeeee eeeeeeeeee.

Me e eeee ee eee eeeeee 88 (8.888eeee, 8 eeeee) ee MM8Me8 (8.8eM), eeeee eeeee eeee eeeeeeeeee eeeeeeee ee 8°M, eee eeeee e 8.8M eeee ee Me8Me ee eeeeeeee (8.888eeee, 8 eeeee). Mee eeeeeeee ee eee eeeeeeee eee eeeeeeee ee MMM eee eeee ee eee eeeeeeee (eeeee 88e), eee eeeeeee eee eeeeee ee ee eee eeee. Mee eeeeee ee eeeeeeeeeeeeee eee eeeeeeeee eeee MeMM, eee eeee e eee. eeee ee eeeeee eeeeeeeee eeeeeeee ee MeMMe/M8M (8:8) eee eeeee ee eeeeeeee eee eeeeeeee eeeee. Mee eeeeeee eeeee eee eeeeeeeee, eee eeeeeee eeeee eee eeeeeeeee eeee MeMMe (8 × 8eM), eee eee eeeeeeee eeeeeee eeeeeeeee eeee eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee ee eeeeeee eee eeeeeee eeeeeee 88. Mee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee.

(8M)-8,8,8-Meeeeeeee-8-eeeeeeeeeeeee-8,8-eeee (88):[‌88‌]

MMMMMMM: Meee eeeeeeeeeeeeeeeee ee eeeeee eeeeeeeeee.

Me e eeee ee (8M)-8-(eeeeeeeeeeeeeee)eeeeee-8-eee (8.88e, 8.8eeee) ee MM8Me8 (8eM) eee eeeee e 8.8M eeee ee Me8Me (88eeee) ee eeeeeee ee 8°M. Mee eeeeeee eee eeeeeee ee eeeee ee ee, eeeeeee eee 88e, eee eeee eeeeeeee eeee 8M MMe. Mee eeeeeee eeeee eee eeeeeeeee, eee eeeeeee eeeee eee eeeeeeeee eeee MeMMe, eee eee eeeeeeee eeeeeee eeeeeeeee eeee eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee ee eeeeeee eee eeeee eeeeeee, eeeee eee eeeeeeee ee MMM (eeeeee eee) ee eeeeee 88 ee eeeee eeeeeeee; eeeee: 8.88e (88%).

References


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