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. 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 1.

Facioselective glycal epoxidation by DMDO

glycal react conda epoxide α:β
graphic file with name nihms281802t1.jpg
glucal		 A graphic file with name nihms281802t2.jpg 10:1
B 10:1b
graphic file with name nihms281802t3.jpg
galactal		 A graphic file with name nihms281802t4.jpg >20:1
B 20:1b
graphic file with name nihms281802t5.jpg
allal (2)		 A graphic file with name nihms281802t6.jpg <1:20
graphic file with name nihms281802t7.jpg
allal, 4,6-acetal (1)		 A graphic file with name nihms281802t8.jpg <1:20
B 1:10b,c
graphic file with name nihms281802t9.jpg
gulal (4)		 A graphic file with name nihms281802t10.jpg 3:2
graphic file with name nihms281802t11.jpg
gulal 4,6-acetal (6)		 A graphic file with name nihms281802t12.jpg 3:1
B 1:1b,c
a

Reaction conditions: (A) DMDO (3 equiv), −55 °C, 2 days; (B) DMDO (2 equiv), 0 °C, 1 hour.

b

See Ref. 5.

c

Ratio obtained using C3 silyl ether.