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. Author manuscript; available in PMC: 2011 Nov 24.

Published in final edited form as: J Am Chem Soc. 2010 Nov 2;132(46):16403–16416. doi: 10.1021/ja105129p

Table 1.

Oxidation of Alcohol 14

Entry	Conditions	Yield^b
1	TPAP(0.1 equiv), NMO (3 equiv), 4A M.S., CH₃CN	65%
2	TPAP(0.1 equiv), NMO (2 equiv), 4A M.S., CH₃CN	67%
2	TPAP(0.1 equiv), NMO (2 equiv), 4A M.S., DCM	56–70%
3	TPAP(0.08 equiv), NMO (2 equiv), 4A M.S., DCM	74%^a
4	TPAP(0.1 equiv), NMO (1.5 equiv), 4A M.S., DCM	77%^a
5	TPAP(0.05 equiv), NMO (1.5 equiv), 4A M.S., DCM	77%^a
6	DMP(3 equiv), NaHCO₃ (20 equiv), DCM	88% (0.83 g scale)

^a

The reaction did not give full conversion.

^b

Isolated yield.