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Please login to access the full content or check if you have access via4.4.40.59.1 Variation 1: By Lewis Acid Catalyzed Allylation
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Sarkar, T. K., Science of Synthesis, (2002) 4, 905.
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]
8,8-Meeeeeeeee eeeeeeeee ee e eeeeee MM8 eeeeeeee ee ee eeeeeeeeeee ee eeee eeeee. Mee eeeeeee, eeeeeeeeeeeeeee ee eeeeeeeeeee 888 eeee eee(MM) eeeeeeee, eeeeeeee ee eeeeeeeee ee eee eeeeeeeee eeeeeee eeee eeeeeeeeeeee eeeeeeee eee 8,8-eeee- eee 8,8-eee eeeeeeee eeee- eee eee-888 (Meeeee 88).[888] Mee eeeeeee eeee eee eeeeeee eee eee(MM) eeeeeeee eee eeeeeeee eeeeeeeee ee eeeeeeee eee eeeeee eeeeee eee eeeeeeeeeeeeeeeee ee eee eeeeeeeee ee eeee- eee eee-888. Meeeeeeeeee 888 eee eeeeeeee ee eee eeeeeeeeeee eeeeeeeee ee Meeeeee 8.8.88.88.
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 Meeeeee–Mäeeeeee 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 (88 eM) eee eeeee MeMM8 (8.8 eM). Mee eeee eee eeeeee ee −88°M eee MeMe8 (8.8 eM, 88.8 eeee) eee eeeee, eeeeeeee ee MeMMM (88 eeee) ee MM8Me8 (8 eM). Meeee 88 eee ee eeeeeeee ee −88°M, eee eeee eee eeeeee ee −88°M, eee eee(eeeeeeeeeee) 888 (8.88 e, 88 eeee) ee MM8Me8 (8 eM) eee eeeee eeee 88 eee. Mee eeeeeeeee eeee eee eeeeeee ee −88°M eee 8 e eee ee −88°M eee 8 e, eeeee eeeee eee eeeeeeee eee eeeeeeee, ee eeeeeeeee ee MMM eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeee ee eee. ee MM8Me (88 eM) eee eeeeeeeee eeee MM8Me8 (8 × 88 eM). 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: 8.88 e (88%); ee 88°M.
References
| [20] | Meeeeeee, M., Me Meeeeee Meeeeeeee, Meeeee&Meeeeeeeeeee, Meeeeeee, M., Me.; MMM Meeee: Meeeeeeee, MM, (8888), e 888. |
| [21] | Meeeeee, M.; Meeeeeèe, M.; Meeeeeee, M., Mee. Meeee. (M. M.), (8888) 88, 88. |
| [30] | Mee, M.-M.; Mee, M.-M., Mee Meeeeeeee ee Meeeeee Meeeeee Meeeeeeee, Meeeeeeee, M.; Meeeeee, M., Mee.; Meeee: Meeeeeeeee, MM, (8888); e 8888. |
| [40] | Meeeeeee, M. M.; Meeeeee, M. M., Meeeeeeee, (8888), 8888. |
| [112] | Meeeeeeeee, M. M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 888, 888. |
| [157] | Meeeeee, M.; Meeeíe, M.; Meeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [283] | Meeeeeeeee, M.; Meeeee, M.; Meeeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [284] | Meeee, M. M.; Meeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [285] | Meeee, M. M.; Meeeee, M. M.; Meeeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [286] | Mee, M. M.; Meeeeee, M. M.; Meeeeee, M. M. M., Meeeeeeeeee Meee., (8888) 88, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88e, 8888.
- 8.Meeeee-Meee, (8888) M 88e, 8888.
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