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. Author manuscript; available in PMC: 2021 May 1.
Published in final edited form as: J Org Chem. 2020 Apr 20;85(9):6044–6059. doi: 10.1021/acs.joc.0c00535

Table 7.

Tautomerization with TFA and DBU

additive (equiv) time (h) 9c′/9c
none 0.5 55:45
none 18 55:45
TFA (3) 0.5 43:57
TFA (3) 18 0:100
DBU (0.5) 0.5 22:78
DBU (0.5) 18 0:100

Methyl (3aS,6aS)-5-Benzyl-3-(2-nitrophenyl)-3a,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole-6a(1H)-carboxylate (9d).