Regioselective Ring Opening of Di-isopropylsilylenes Derived from 1,3-Diols with Alkyl Lithium Reagents

The selective alkyl lithium-induced ring opening of 1,3-di-isopropylsilylenes is described. The reaction affords a differentially substituted 1,3-diol bearing a silane that resides at the oxygen in the more sterically demanding position. The reaction can be highly selective with a regiochemical pref...

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Bibliographic Details
Published in:Organic letters 2015-11, Vol.17 (21), p.5196-5199
Main Authors: Chando, Katelyn M, Bailey, Patricia A, Abramite, Joseph A, Sammakia, Tarek
Format: Article
Language:English
Subjects:
Alcohols - chemistry
Indicators and Reagents
Lithium - chemistry
Molecular Structure
Silanes - chemistry
Stereoisomerism
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Summary:The selective alkyl lithium-induced ring opening of 1,3-di-isopropylsilylenes is described. The reaction affords a differentially substituted 1,3-diol bearing a silane that resides at the oxygen in the more sterically demanding position. The reaction can be highly selective with a regiochemical preference up to >50:1 and likely proceeds via an alkoxy-silane intermediate. This intermediate can by trapped by methyl iodide to provide the corresponding silyl methyl ether, wherein the silane again resides at the oxygen in the more sterically demanding position.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02529