. Author manuscript; available in PMC: 2012 Apr 15.

Published in final edited form as: J Org Chem. 2011 Mar 18;76(8):2532–2547. doi: 10.1021/jo102382r

TABLE 3.

Facioselectivities of deoxyglycal epoxidation by DMDO

4-DP	react cond^a	α:β
11	A	20:1
3	A	<1:20
9	A	1:1
8	A	1:2^b
15	B	>20:1
14	A	4:1

Reactio conditions: (A) DMDO (3 equiv), −55 °C, 2 days; (B) DMDO (3 equiv), −55 °C, 1 day.

Determined by ¹H NMR peak integration.