Table 3.
Exploration of isomerization of 85
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conditions | results | |
1 | Pd/C, H2 (activation), EtOAc, r.t. | no reaction, 85 recovered, no dimer |
2 | (PhCN)2PdCl2, benezene, 60 °C, | dimer and trace 87, acetal deprotection |
3 | (Ph3P)3RhCl, Et3SiH, 100 °C | dimer, hydrosilation, trace 87 |
4 | Co(salen)Cl, PhSiH3, r.t. to 60 °C | dimer |
5 | Co(dmgH)2 •2 H2O, PhSiH3, 60 °C | dimer, reduction, and trace 87 |
6 | RhCl3 •xH2O (0.2 equiv.), EtOH, 100 °C | 20% yield of 87. dimer, acetal hydrolysis |
7 | using Mannich base as substrate K2CO3 (2 equiv.) | 33% yield of 87. EtOH addition no acetal hydrolysis |