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Concerning the selective protection of (Z)-1,5-syn-ene-diols and (E)-1,5-anti-ene-diols as allylic triethylsilyl ethers.

ABSTRACT: Treatment of unsaturated 1,5-diols 2 with TES-Cl (1.1 equiv), imidazole, and catalytic DMAP in 1:1 CH2Cl2-DMF at -78 degrees C effects selective silylation of the allylic alcohol with >95:5 chemoselectivity when the allylic and homoallylic alcohols are in similar steric environments.

SUBMITTER: Hicks JD

PROVIDER: S-EPMC2504016 | biostudies-literature | 2007 Dec

REPOSITORIES: biostudies-literature

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Concerning the selective protection of (Z)-1,5-syn-ene-diols and (E)-1,5-anti-ene-diols as allylic triethylsilyl ethers.

Hicks Jacqueline D JD Huh Chan Woo CW Legg Ashley D AD Roush William R WR

Organic letters 20071121 26

Treatment of unsaturated 1,5-diols 2 with TES-Cl (1.1 equiv), imidazole, and catalytic DMAP in 1:1 CH2Cl2-DMF at -78 degrees C effects selective silylation of the allylic alcohol with >95:5 chemoselectivity when the allylic and homoallylic alcohols are in similar steric environments. ...[more]

PMID: 18027963

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