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. Author manuscript; available in PMC: 2008 Dec 20.
Published in final edited form as: Org Lett. 2007 Nov 21;9(26):5621–5624. doi: 10.1021/ol702588h

Table 3.

Selective Protection of (E)-1,5-anti-diols

entry substrate
(R = H)		 producta
(R = SiEt3)		 yieldb,c allylic:
homoallylic
1 graphic file with name nihms-60246-t0009.jpg 19 66% 95:5
2 graphic file with name nihms-60246-t0010.jpg 21 66% >97:3
3 graphic file with name nihms-60246-t0011.jpg 23 79% >97:3
4 graphic file with name nihms-60246-t0012.jpg 25 44% 84:16
5 graphic file with name nihms-60246-t0013.jpg 27 58% 77:22
a

Reactions were performed by treating a solution of the 1,5-diol (1 equiv), imidazole (1.15 equiv), and DMAP (0.05 equiv) in CH2Cl2-DMF (1:1, 0.1 M) at −78 °C with TES-Cl (1.1 equiv)

b

Combined yield of mono-TES esters (allylic and homoallylic)

c

bis-TES ethers were obtained as follows: entry 1, 20%; entry 2, 2%, entry 3, 2%, entry 4, 16%, entry 5, 16%.