Table 2.
Variation of nitriles and alcohols.a
 | |||||
| # | R1 = Me | R1 = Bn | R1 = Ph | R1 = Vinyl | |
| R2−OH | Product, Yield [%] | ||||
| 1 | Fluorenylmethanol (1) | 2, 83 | 3, 86 | 4, 44 | 5, 52 (67b) |
| 2 | Me(CH2)9OH (6) | 7, 80 | 8, 85 | 9, 23 | 10, 29 (40b) |
| 3 | Cl(CH2)6OH (11) | 12, 84 | 13, 90 | 14, 27 | 15, 38 (16b) |
| 4 | Et[O(CH2)2]2OH (16) | 17, 75 | 18, 85 | 19, 26 | 20, 23 (19b) |
| 5 | p-NO2C6H4CH2OH (21) | 22, 90 | 23, 78 | 24, 39 | 25, 85 |
| 6 | p-HO2CC6H4CH2OH (26) | 27, 88 | 28, 87 | 29, 31 | 30, 64 |
| 7 | HO(CH2)6OH (31) | 32, 32 (33, 19c) | 34, 46 (35, 37c) | — | — |
| 8 | EtO2C(CH2)5OH (36) | 37, 21 | 38, 16 | 39, 10 | 40, 7 |
| 9 | Z-NH(CH2)4OH (41) | 42, 13 | 43, 13 | 0 | 44, 14 |
| 10 | cyHexOH (45) | 46, 15 | 47, 25 | — | — |
| 11 |
 (48) |
0 | 0 | — | — |
| 12 | PhOH (49) | 0 | — | — | — |
| 13 | p-NO2C6H4OH (50) | 0 | — | — | — |
| 14 | 3,4,5-Trimethoxyphenol (51) | 0 | — | — | — |
| 15 | p-MeOC6H4CH2OH (52) | 0 | 0 | 0 | 0 |
aAlcohol (1 equiv), TMSOTf (2 equiv) dissolved in the nitrile (4 mL/mmol alcohol), rt, 65 h. bTMSOTf (2 equiv) and nitrobenzene (1 equiv) were added. cTMSOTf (4 equiv) was added. Yield of the monoacylated by-products 33 and 35, respectively, in parentheses.