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. Author manuscript; available in PMC: 2016 Jan 5.
Published in final edited form as: Org Lett. 2014 Jun 27;16(14):3636–3639. doi: 10.1021/ol501236a

Table 1.

Optimizing the Reaction Temperature for the Henry/Ketalization Sequence

graphic file with name emss-66353-t0005.jpg

entrya temp (°C) yieldb (%) drc
1 rt 50 3:1
2 0 61 8:1
3 −20 80 >20:1
a

The reaction was performed on a 0.2 mmol scale.

b

Combined yield of isolated product as a mixture of diastereomers after flash chromatography.

c

Diastereomeric ratio; major-(2S,3S,4S,5R,6R) vs minor-(2S,3S,4S,5S,6S) diastereomer determined by 1H NMR.