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Please login to access the full content or check if you have access via5.2.25.5.2 Variation 2: By Metal-Catalyzed Addition of a Trialkyltin Hydride
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Crisp, G. T., Science of Synthesis, (2003) 5, 529.
The hydrostannylation of methyl propiolate under catalysis by dichlorobis(triphenylphosphine)palladium(II) at room temperature is reported to give a 90% yield of 28 (R1 = CO2Me) as a result of a distal syn addition (Scheme 13).[35] Under the same conditions, propargyl alcohols and ethers give mixtures of 28 and 29 resulting from both distal and proximal syn addition.[35] The use of tetrakis(triphenylphosphine)palladium(0) for the addition of tributylstannane to ethyl propiolate at room temperature gives 29 (R1 = CO2Et) as the major product (80% isolated yield).[36]
8-Meeeeeeeeeee eeeeeee eeeeeee eeeeee ee eeeeeeee eeeeeeeeeeeeeee eeeee eeee 8 eeeeeeeeeee ee eeeeeeeeeeeeeeee ee eee eeeeeeee ee e eeeeeeeee eeeeeeee ee eeee eee M-eeeeeeeeeeeeeee ee eeeeeeeee eeeee ee e eeeeee ee e eeeeeeeeeeeeeeee eee eeeeeeee.[88] Meee eeeeee eeeeeeee ee eeeeeee eee eeeeeeee ee eee eeeeeeeeeeeeeeee, eeeeeeee ee e eeeeeeeee-eeeeeeeee eeeeee–eeeeeee eeeeeeeee.
Mee eeeeeeeeeeeee eeeeeee, eeee eeeeee eeeeeee eee eee eeeeeeee ee eeeee eeeeeee ee eeeeeeeeeeee ee eee eeeeeeeee eeeeeeee eee eeeeeeeee eee eeeeeeeeeeeeee ee eee eee eeeeeee eeeeeeee. Meeee eeeeeeeeeeee ee eee eeeeee ee eeeee eeeeeeeee eeeeeee ee eee eeeeeeeee eeeeeeee eeeee eeeeeeee eeee eeee eee eeeee eeeeeee eeeee ee eeeeee eeeeee ee eee eeeee eeeeee eeeeeeeeeee, ee ee eee eeeeeeeee ee 88 (M8 = eMe; M8 = Me) (Meeeee 88).[88] Mee eeeeeeee ee e eeeeeeeeeee (eeeeee eeeeeeee-eeeeeeee ee -eeeeeeeeeee) ee eee α-eeeeeeee ee eee eeee eeee ee eeeeeeeeeee eeeeee eee eeeeeeeeeeeeee eeeeeeeee ee 88 (M8 = 8-MeM8M8; M8 = M) ee eee eeeeeeee ee e eeeeeeeee eeeeeeee (Meeeee 88).[88]
Mee eeeeeeeeeeeeeeeee ee M-eeeeeeeeeeee eeee eeeeeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeeeee eeeee eeeeeeeeeeeee eee eeeeeeeeeee 88 [M8 = M-MM=MMMe; M8 = (MM8)8MM], eeeeeeeeeee ee e eeeee eeeeee ee 88 [M8 = M-MM=MMMe; M8 = (MM8)8MM], eeeeeee eeee M-eeeeeeeeeeee eeeee eee eeee eeeeeeeeee eeee eeeeeeeeeee 88 [M8 = M-MM=MMMe; M8 = (MM8)8MM] ee eeeeee ee eeee eeeee (Meeeee 88).[88,88]
Mee eeeeeeee ee eeeeeeeeeeeeeeee ee e eeeeeeee eeeeee ee eee eeeeeeee ee eeeeeeeee(MM) eeeeeeee eeeeeeeeeeeeeeeee eeeeeee eee eeeeeeeeeeeee M-eeeeeeeeeeeeeee.[88] Mee eee ee eeeeeeee eeeeeeee eeeee e eeeeeee ee M- eee M-eeeeeeeeeeeeeeee. Mee eeeeeeee ee ee eeeee eeeeeeeeeeeee eee ee eeeeeeeee, eeeeeeee eeee eee eeeeeeeeee eeeee ee eeeee eee eeeeeeeee eeeeeeeeeeee ee eee Meeee eeee eeeeeeee ee eee eeeeee eeee. M eeeeeeeeeeee ee eeee eeeeeeeee eeeeeeee eee ee eeee eeeeeeeeee ee eee eeeeeeeeeeeeeeee eeee eeeeeeeeeeeeeeeeeeeeee, eeeeeeeeeeeeee, eee eeeeeeeee(MM) eeeeeeee.[88]
8-Meeeeeeee-8-eeee eeeeeee eeeee eeeeeeeeeeeeeeeee eeee eeeeeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeeee, eeeeeeeee ee eee eeeeeeee eeee eeeeeeeeeee eeeeeeeee ee eee eeeeeeeeeee 88 (M8 = MMM8MMe; M8 = Me) (Meeeee 88).[88] Meeeeeeeee eee eeee ee eee eeeee eeeeeeeeeee M8 eeeeeeeee eee eeeeeeeeee ee eeeeeeeeeee 88 (M8 = MMM8MMe). Meeeeeeeeeeeeeeee ee eee eeeeeeeeeeeee 8-eeeeeeeeee-8-eeee eeeee e eeeeeeeeeeeeeee eee eeeeeeee ee eeeee ee eee eeeeeeeee eeeeeeeeeee.[88]
Meeeee 88 Meeeeeeee-Meeeeeeee Meeeeeeeeeeeeeeee ee Meeeeee[88,88,88–88,88]
| M8 | Me Meeeeeee | Meeee (%) ee 88 | Meeee (88/88) | Mee |
|---|---|---|---|---|
| MM8MM | MeMe8(MMe8)8 | 88 | 8:88 | [88] |
| MM8Me | MeMe8(MMe8)8 | 88 | 888:8 | [88] |
| MM8Me | Me(MMe8)8 | 88 | 8:888 | [88] |
| MM8MMMM | MeMe8(MMe8)8 | 88 | 8:88 | [88] |
| M8 | M8 | Me Meeeeeee | Meeee (%) ee 88 | Meeee (%) ee 88 | Mee |
|---|---|---|---|---|---|
| eMe | Me | MeMe8[M(8-Mee)8]8 | 88 | 8 | [88] |
| 8-MeM8M8 | M | MeMe8(MMe8)8 | 8 | 88 | [88] |
| M-MM=MMMe | (MM8)8MM | Me(MMe8)8 | 88 | 88 | [88,88] |
| M-MM=MMMe | (MM8)8MM | Me(MMe8)8 | 8 | 88 | [88,88] |
| MMM8MMe | Me | Me(MMe8)8 | 88 | 88 | [88] |
Meeeeeeeeeee Meeeeeeee
Meeee 8-(Meeeeeeeeeeeeee)eeee-8-eeeeee (88, M8 = MM8Me); Meeeeee Meeeeeeee:[88]
M eeeeeeee eeee ee Me8MeM (88.8 e, 88.8 eeee) ee eee MMM (888 eM) eee eeeee ee e eeee ee eeeee eeeeeeeeee (8.88 e, 88.8 eeee) eee Me(MMe8)8 (8.88 e, 8.8 eeee) ee MMM (888 eM) eeee e eeeeee ee 8 e. Mee eeeeeeeee eeeeeee eee eeeeeee eee 8 e ee ee eeeee eeeee. Mee MMM eee eeee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeee eeee eeeeee (8.8 M). Meeee 88 e, eee eeeeeee eee eeeeeeee eeeeeee Meeeee eee eee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeee eeee eeeeee (888 eM), eee eeeeeeeee eeee eee eeeee eeeeeeee eeeeeee Meeeee, eee eee eeeeeeee eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeee eeeeeeee ee eeeeeeeeee eeeeeeeeeeee ee eeee eee eeeeeee ee e eeeeeeeee eee; eeeee: 88.88 e (88%); ee 888–888°M/8.88 Meee.
References
| [35] | Meeee, M. M.; Meeee, M.; Meeeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 888. |
| [36] | Meeeeee, M.; Meeeeee, M.; Me Meeeee, M.; Meeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [37] | Meeee, M. M. M.; Meeeeeeee, M.; Me, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [38] | Meeeeee, M.; Meeeee, M. M., Meeeeee, (8888), 888. |
| [39] | Meeee, M.; Me Meeeee, M.; Meeee, M., Meeeeee, (8888), 888. |
| [40] | Meeee, M.; Meeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [41] | Meeee, M.; Meeee, M., Meeeeee, (8888), 888. |
| [42] | Meee, M.; Mee, M.-M.; Meeee, M.; Meeeeeee, M., M. Meee. Mee., Meee. Meeeee., (8888), 8888. |
| [43] | Meeeeeeee, M.; Mee, M.-M.; Meeeeeee, M., Meee. Meeeee. (Meeeeeeee), (8888), 88. |
| [44] | Meeeee, M.; Meeeeeeee, M., Meeeeeeee, (8888), 8888. |
| [45] | Meeee, M.; Me, M., Meeee. Meeeee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 8888.
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