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. Author manuscript; available in PMC: 2011 Jul 21.
Published in final edited form as: Angew Chem Int Ed Engl. 2010 Aug 9;49(34):5894–5897. doi: 10.1002/anie.201002281

Table 2.

Tertiary ether substrates in stereoselective cyclization reactions.[a]

Entry Substrate[b] Product t [h] d.r.[c] Yield [%][d]
1 graphic file with name nihms308194t19.jpg
23 		graphic file with name nihms308194t20.jpg
24 		2.5 100:0 79
2 graphic file with name nihms308194t21.jpg
25 		graphic file with name nihms308194t22.jpg
26 		2 15.7:1 95
3 graphic file with name nihms308194t23.jpg
27 		graphic file with name nihms308194t24.jpg
28 		0.5 100:0 76
4 graphic file with name nihms308194t25.jpg
29 		graphic file with name nihms308194t26.jpg
30 		0.3 – 88
5[e] graphic file with name nihms308194t27.jpg
31 		graphic file with name nihms308194t28.jpg
32 		5 100:0 81
6[f] graphic file with name nihms308194t29.jpg
33 		– – – –
[a]

Typical procedure: a solution of the substrate and 2,6-dichloropyridine in 1,2-dichloroethane was treated with DDQ and stirred for the indicated time period.

[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.

[e]

Reaction was conducted at −30°C.

[f]

no reaction occurred.