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. Author manuscript; available in PMC: 2024 Sep 9.
Published in final edited form as: J Org Chem. 2024 Aug 12;89(17):11891–11908. doi: 10.1021/acs.joc.4c01116

Table 3.

Exploration of isomerization of 85

graphic file with name nihms-2019312-t0051.jpg
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