Synthesis of allylic and homoallylic alcohols from unsaturated cyclic ethers using a mild and selective C-O reduction approach

Daniel J. Mack; Boying Guo; Jon T. Njardarson

doi:10.1039/c2cc33551d

Synthesis of allylic and homoallylic alcohols from unsaturated cyclic ethers using a mild and selective C-O reduction approach

Daniel J. Mack, Boying Guo, Jon T. Njardarson

Research output: Contribution to journal › Article › peer-review

42 Scopus citations

Abstract

Unsaturated cyclic ethers can be mildly and selectively reduced with catalytic amounts of B(C₆F₅)₃ in the presence of an alkylsilane. The allylic position is preferentially reduced with minimal or no scrambling of olefin geometry. For electronically equivalent substrates, steric factors guide the reducing agent to the least substituted site.

Original language	English (US)
Pages (from-to)	7844-7846
Number of pages	3
Journal	Chemical Communications
Volume	48
Issue number	63
DOIs	https://doi.org/10.1039/c2cc33551d
State	Published - Jul 11 2012

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/c2cc33551d

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title = "Synthesis of allylic and homoallylic alcohols from unsaturated cyclic ethers using a mild and selective C-O reduction approach",

abstract = "Unsaturated cyclic ethers can be mildly and selectively reduced with catalytic amounts of B(C6F5)3 in the presence of an alkylsilane. The allylic position is preferentially reduced with minimal or no scrambling of olefin geometry. For electronically equivalent substrates, steric factors guide the reducing agent to the least substituted site.",

author = "Mack, {Daniel J.} and Boying Guo and Njardarson, {Jon T.}",

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T1 - Synthesis of allylic and homoallylic alcohols from unsaturated cyclic ethers using a mild and selective C-O reduction approach

AU - Mack, Daniel J.

AU - Guo, Boying

AU - Njardarson, Jon T.

PY - 2012/7/11

Y1 - 2012/7/11

N2 - Unsaturated cyclic ethers can be mildly and selectively reduced with catalytic amounts of B(C6F5)3 in the presence of an alkylsilane. The allylic position is preferentially reduced with minimal or no scrambling of olefin geometry. For electronically equivalent substrates, steric factors guide the reducing agent to the least substituted site.

AB - Unsaturated cyclic ethers can be mildly and selectively reduced with catalytic amounts of B(C6F5)3 in the presence of an alkylsilane. The allylic position is preferentially reduced with minimal or no scrambling of olefin geometry. For electronically equivalent substrates, steric factors guide the reducing agent to the least substituted site.

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JO - Chemical Communications

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ER -

Synthesis of allylic and homoallylic alcohols from unsaturated cyclic ethers using a mild and selective C-O reduction approach

Abstract

ASJC Scopus subject areas

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