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. Author manuscript; available in PMC: 2020 Mar 23.
Published in final edited form as: Nat Chem. 2019 Sep 23;11(10):890–898. doi: 10.1038/s41557-019-0338-2

Table 1.

Nucleophilic cleavage of the α-ketoimine 25 and the α-diketone 26.

graphic file with name nihms-1537872-t0007.jpg
entry substrate nucleophile product(s) (yield)a
1 25 methanolb 30a (42%) + 30d (~42%)e
2 25 waterc 30b (51%)
3 25 pyrrolidined 30c (36%)
4 26 methanolb 30a (45%) + 30e (41%)
5 26 waterc 30b (49%) + 30f (25%)
6 26 pyrrolidined 30c (41%)
a

Isolated yield after purification by flash-column chromatography.

b

25 or 26 (1 equiv), NaHCO3 (9.0 equiv), methanol, 23 °C, 48 h (for 25 and 26).

c

25 or 26 (1 equiv), tetrahydrofuran–saturated aqueous sodium bicarbonate solution (1:1, v/v), 23 °C, 48 h (for 25), 72 h (for 26).

d

25 or 26 (1 equiv), pyrrolidine (14 equiv), dichloromethane, 23 °C, 48 h (for 25), 72 h (for 26).

e

Estimated by HPLC analysis of the product mixture.