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. Author manuscript; available in PMC: 2018 Nov 22.
Published in final edited form as: Org Biomol Chem. 2017 Nov 22;15(45):9570–9574. doi: 10.1039/c7ob02283b

Table 2.

Scope of XtalFluor-E® catalyzed synthesis of N,O-acetals.a

graphic file with name nihms918582u3.jpg

Entry Enamide N,O-acetal Yield (%)
1 graphic file with name nihms918582t1.jpg graphic file with name nihms918582t2.jpg 95
2 98
3 graphic file with name nihms918582t3.jpg graphic file with name nihms918582t4.jpg 98
4 95
5 80
6 40
7 98b
8 85
9 graphic file with name nihms918582t5.jpg graphic file with name nihms918582t6.jpg 85c
10 graphic file with name nihms918582t7.jpg graphic file with name nihms918582t8.jpg 98
11 graphic file with name nihms918582t9.jpg graphic file with name nihms918582t10.jpg 91
12 72
13 graphic file with name nihms918582t11.jpg graphic file with name nihms918582t12.jpg 60
14 graphic file with name nihms918582t13.jpg graphic file with name nihms918582t14.jpg 98
15 graphic file with name nihms918582t15.jpg graphic file with name nihms918582t16.jpg 71
98d
16 graphic file with name nihms918582t17.jpg graphic file with name nihms918582t18.jpg 83
17 graphic file with name nihms918582t19.jpg graphic file with name nihms918582t20.jpg 86
18 graphic file with name nihms918582t21.jpg graphic file with name nihms918582t22.jpg 98
19 graphic file with name nihms918582t23.jpg graphic file with name nihms918582t24.jpg 98e
21 graphic file with name nihms918582t25.jpg graphic file with name nihms918582t26.jpg 94
21 98d
a

Reactions were performed at room temperature (0.1 mmol), reported yields are isolated unless otherwise indicated;

b

1.1 equivalents of nucleophile was used, requiring 48 h for reaction completion, resulting in the same yield;

c

Reaction was performed at 1.0 mmol scale;

d

Yield was determined by 1H-NMR with methyl t-butyl ether as internal standard;

e

HFIP:methanol (9:1 v:v) was used as solvent.