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4.4.40.59.1 Variation 1: By Lewis Acid Catalyzed Allylation

DOI: 10.1055/sos-SD-004-00909

Sarkar, T. K.Science of Synthesis, (20024905.

Lewis acid catalyzed allylation of aldehydes and ketones with allylsilanes can provide homoallyl alcohols.[‌20‌,‌21‌,‌30‌] These reactions usually require stoichiometric amounts of Lewis acid, although a catalytic version is also possible (Scheme 4).[‌40‌] Diastereocontrol in the reactions of but-2-enylsilanes with aldehydes was shown in Scheme 2. Remarkably, a single diastereomer of dienediol 231 is obtained by the titanium tetrachloride catalyzed reaction of an isomeric mixture of allylsilanes 230 with pentanal (Scheme 88).[‌283‌] Incidentally, the pure E,E-isomer of 230 is available by the synthetic method described in Section 4.4.40.21 (Scheme 36).

Meeeee 88 Meeeeeeeeeeeeee Meeeeeeee ee 8,8-Meeeeeeeeeeeeeeeee-8,88-eeee[‌888‌]

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Meeeee 88 8,8-Meeeeeeeee Meeeeeeee ee eee Meeeeeee ee e 8-Meeeeeeee-8-eeeeeeeeee[‌888‌]

Meeeeeeee, eee eeeeeeee ee ee eeeeeeeeeee ee ee eeeeeeee eee ee eeeeeeee eeee e eeeeeeeeee eeeeeeee ee eeee eeeeeeeeeeeeeee eeeeeeeeeee eeeeeeeeeee, eee eeeeeee, eee eeeeeeeeeee ee 888 (Meeeee 88).[‌888‌] Meee eeeeeeeeeee ee eeeeeeeee eeee eeeeeeeee ee eee eeeeee ee eeeeeeeeeee ee eeeeeeeeeeeeeee 88 eeeeeeeee ee Meeeeee 8.8.88.8.8.

Meeeee 88 Meeeeeeee ee Meeeeeeeeeeeeee Meeeeeeeeee Meeeeeeeeee[‌888‌]

Mee Meeee eeee eeeeeeee eeeeeeeeee eeeeeeeee eee eeee ee eeeeeeeee eeeeeeeeeeeeeeee,[‌88‌,‌88‌,‌88‌] eee eeeeeee, eee eeeeeeeee ee eeeeeeeeee eeeeeeeee 888 eee 888 (Meeeee 88).[‌888‌,‌888‌] Meeee eee eeeeeeeeeee ee eeeeeeeeeee 888 eeee eeeeeeeee ee eee MeeeeeeMäeeeeee eeeeeeee (Meeeeee 8.8.88.88),[‌888‌] eeeeeeeeeee 888 eee eeee ee e eeeeeeeeeeeeeee eeeeeeeeeeeeee ee eeeeee (Meeeeee 8.8.88.88).

Meeeee 88 Meeee Meee Meeeeeeee Meeeeeeeeeeeee Meeeeeeeee Meeeeeeee[‌888‌,‌888‌]

Meee ee eeeeeeeeeeeeee eeeeeeeeee ee eeee e eee eeeeeee ee eee eeeeeeeee ee eeeee eeeeeeee eeeeeee, eee eeeeeee, 888 (Meeeee 88).[‌888‌] Meeeeeeeeee 888, eeee eee eeee eeeeeeeeeee, ee eeeeeeeee ee eee eeeeee ee eeeeeeeee eeeeeeeee ee Meeeeee 8.8.88.88.

Meeeee 88 Meeeeeeee ee Meeee Meeeeeee Meeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

(8MM,8MM,8MM,88MM)-8,8-Meeeeeeeeeeeeeeeee-8,88-eeee (888):[‌888‌]

M eeeee-eeeeee eeeee eeeeeeee eeee e eeeeeeeeeee, eeeeee eee, eeeeeeee eeeeeeee eee, eee eeeee eeeeee eee eeeeeee eeee eeeee MM8Me8 (88eM) eee eeeee MeMM8 (8.8eM). Mee eeee eee eeeeee ee 88°M eee MeMe8 (8.8eM, 88.8eeee) eee eeeee, eeeeeeee ee MeMMM (88eeee) ee MM8Me8 (8eM). Meeee 88eee ee eeeeeeee ee 88°M, eee eeee eee eeeeee ee 88°M, eee eee(eeeeeeeeeee) 888 (8.88e, 88eeee) ee MM8Me8 (8eM) eee eeeee eeee 88eee. Mee eeeeeeeee eeee eee eeeeeee ee 88°M eee 8e eee ee 88°M eee 8e, eeeee eeeee eee eeeeeeee eee eeeeeeee, ee eeeeeeeee ee MMM eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeee ee eee. ee MM8Me (88eM) eee eeeeeeeee eeee MM8Me8 (8×88eM). Mee eeeeeeee eeee eeeeee eeeee eeeeeee, eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee, eeeeeee/Me8M 8:8); eeeee: 8.88e (88%); ee 88°M.

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