Table 1.

Synthesis of tertiary ethers from oxidation of allylic and benzylic ethers.^[a]

Entry	Substrate[b]	Product	t [h]	d.r.[c]	Yield [%][d]
1	6	7	12	26:1	84
2	8	9	2.5	100:0	86
3	10	11	2	100:0	78
4	12	11	2	100:0	74
5	13	14	0.67	100:0	82
6	15	16	0.5	100:0	84
7	17	18	7	100:0	67
8	19	20	5.5	3:1	85[e]
9[f]	21	22	4	10:1	82

^[a]Typical procedure: a 0.1 M solution of the substrate and 2,6-dichloropyridine in MeNO₂ was treated with DDQ and stirred at 0 °C or at RT for the indicated time period. See the Supporting Information for details on specific reactions.

^[b]See the Supporting Information for details on substrate synthesis.

^[c]d.r. =diastereomer ratio normalized to 100.

^[d]Yields refer to isolated, purified material unless otherwise noted.

^[e]Yield corresponding to the mixture of stereoisomers.

^[f]Reaction was conducted at −60°C in EtNO₂.