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. Author manuscript; available in PMC: 2010 Feb 10.
Published in final edited form as: Angew Chem Int Ed Engl. 2008;47(10):1928. doi: 10.1002/anie.200705267

Table 2.

Scope of the allylic etherification with various alcohols.[a]

graphic file with name nihms173106u2.jpg

Entry R t [h] b:l[b] Yield [%], ee[c] or de
1 Bn 22 99:1 68, 93% ee
2 n-hexyl 40 99:1 71, 91% ee
3[d] n-hexyl 20 84:16 77, 94% ee
4[d] cyclo-hexyl 40 99:1 68, 93% ee
5 N-Boc-4-piperidinyl[e] 50 99:1 66, 90% ee
6 (S)-1-phenylethanol 80 99:1 67, 88% de[f]
7[g] (S)-1-phenylethanol 40 99:1 63, 90% de
8 TBDMS[h] 40 98:2 85, 98% ee
[a]

All times, ratios of b:l, isolated yields and ee or de values are averages from two independent runs.

[b]

Ratio of b:l determined by 1H NMR analysis of the crude reaction mixture.

[c]

Determined by HPLC.

[d]

Alcohols (2.5 mmol) and K3PO4 (2.5 mmol) were used.

[e]

Boc=tert-butoxycarbonyl.

[f]

d.r. 94:6.

[g]

(S,S,S)-L1 was used; d.r.=95:5.

[h]

TBDMS=tert-butyldimethylsilyl.