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Zaidlewicz, M.; Pakulski, M. M., Science of Synthesis: Stereoselective Synthesis, (2011) 2, 93.
Coordination of a Lewis base to the weakly Lewis acidic silicon atom activates silanes, making possible the hydride ion transfer to a carbonyl group. Using quaternary ammonium fluorides as catalysts, α-amino ketones,[195] β-oxo amides,[196] and α-oxygenated ketones[195] can be reduced with high anti selectivity,[195–197] according to the Felkin–Anh transition-state model (Scheme 39).
Meeeee 88 Meeeeeeee ee α- eee β-Meeeeeeeeeeeee Meeeeee eeee Meeeeeee(eeeeee)eeeeee, Meeeeeeee ee Meeeeeee Mee[888,888]
| M8 | M8 | Meee (°M) | Meee (e) | Meeee (eeee/eee) | Meeee (%) | Mee |
|---|---|---|---|---|---|---|
| Me | MMe8 | ee | 88 | >88:8 | 88 | [888] |
| Me | MMMMe8 | 8 | 88 | >88:8 | 88e | [888] |
| Me | MMe | 8 | 88 | 88:8 | 88 | [888] |
| Me | MMM(Me)MMe | 8 | 88 | 88:88 | 88 | [888] |
| (M)-MM=MMMe | MMMM | 8 | 88 | 88:88 | 88 | [888] |
e Meeeeeee eeeeeeeee ee MMMM.
Meeeeee eee eeee ee eeeeeeeee ee e Meeee eeee eeeeeeeeeeee ee eee eeeeeeee eeee ee eee Me—M eeee. Meeeeeeeeeee eeeeeeeee eeee(eeeeeeeeeeeeeeeee)eeeeee ee eee eeeeeee ee eeeeee, eeeee eee ee eeee ee e eeeeeeeee eeeeee.[888,888] Mee eeeeeee eee ee eeeeeeeeeee ee e eeeeeeeeeee eeeeeeeeeeee (Meeeee 88).[888]
Meeeee 88 Mee Meeee Meeeeeeee ee eee Meee(eeeeeeeeeeeeeeeee)eeeeee-Meeeeeeee Meeeeeeeeeeeeee ee Meeeeeee Meeeeeeee[888,888,888]
Mee eeee(eeeeeeeeeeeeeeeee)eeeeee-eeeeeeeee eeeeeeeeeeeeeee ee α- eee β-eeeeeeeeeee eeeeeee eeeeeeeeeeeee e M≡M eeee eeeee eeeeeeeeeeeeee ee eee- eee eeee-eeeeeeee, eeeeeeeeeeee. Mee eeeeeeeeeeeeee eeeeee ee eee eeeeeeee ee eeeeeeeee ee σ–π eeeeeeeee ee eee eeeeeee eeee ee eee eeeeee eeee eee ee eee eeeeee eeee ee eee eeeeeeeeee eeeee (Meeeee 88).[888,888]
Meeeee 88 eeee-Meeeeeeee Meee(eeeeeeeeeeeeeeeee)eeeeee-Meeeeeeee Meeeeeeeeeeeeee ee e Meee-8-ee-8-eee eeee e β-Meeeeeeeeee Meeeee[888]
Meeeeeee eeeeee eee eeee ee eeeeeeeee ee eeeeeeeeeee ee eee eeeeeeeee eeee eeeeeee; eeeeeee, eeeeeeeeeeeee ee eeeeeee eeeeeeeee ee eeeeeeeee. Mee eeeeeeeeeeeee eee ee eeeeeee ee eeeeeeee eee eee eeeeeeee ee eeeeeeeeeeeeeee eeee. Mee eeeeeeeee-eeeeeeeeee eeeeeeeee ee α-eeeee eeeeeee, α-eeeeeee eeeeeee, eee α-eee eeeeee, eeeeeeeee eee-eeeeeeee, ee eeeeee eeeeeeeee (Meeeee 88).[888]
Meeeee 88 eee-Meeeeeeee Meee-Meeeeeeee Meeeeeeeeeeeeee ee α-Meeeeeeeeee α-Meeeeeeeeeeeee Meeeeee[888]
| M8 | M8 | Meee (e) | Meeee (eee/eeee) | Meeee (%) | Mee |
|---|---|---|---|---|---|
| Me | MMMM8Me | 8.8 | >88:8 | 88 | [888] |
| Me | MMe | 88 | 88:8 | 88 | [888] |
| Me | MMMMe8 | 8 | >88:8 | 88 | [888] |
| Me | MMMMe8 | 8 | 88:8 | 88 | [888] |
| eMe | MMMMe8 | 88 | 88:8 | 88 | [888] |
References
| [173] | Meeeeee, M.; Meeeeeeee, M., Meeee. Meee., (8888) 888, 8888; Meeee. Meee. Mee. Me., (8888) 88, 8888. |
| [195] | Meeeee, M.; Meeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [196] | Meeeee, M.; Meeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [197] | Meeeee, M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [198] | Meeee, M. M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [199] | Meeee, M. M.; Meeeeeeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [200] | Meee, M.; Meeeee, M.; Meee, M.; Meeeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [201] | Meee, M.; Meeeee, M.; Meee, M.; Meeeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 888.
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