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. Author manuscript; available in PMC: 2019 Jul 6.
Published in final edited form as: J Org Chem. 2018 Jan 23;83(13):6995–7009. doi: 10.1021/acs.joc.7b02972

Table 1.

Equilibration of acetal 23 to aldehyde 24

graphic file with name nihms945199u5.jpg
entrya additiveb 23/32: 24c
1 66 : 34
2 d 39 : 61
3 CuCl2 75 : 25
4 ZnCl2 41 : 59
5 Cu(OTf)2 36 : 64
6 Zn(OTf)2 30 : 70
7 3 Å MS 32 : 68
8 4 Å MS 29 : 71
9 4 Å MS/Zn(OTf)2 27 : 73
10 4 Å MS/Cu(OTf)2 28 : 72
a

Each entry started from pure acetal 23.

b

Lewis acids were used in 20 mol %; molecular sieves were used in 0.5 g/mmol.

c

Ratio determined by 1H NMR analysis of crude reaction filtrate after 20–24 h.

d

At 50 °C.