期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 136, 期 2, 页码 777-782出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja4110842
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资金
- NSERC of Canada
- Fonds der chemischen Industrie
- Studienstiftung des deutschen Volkes
Novel allyl boron compounds are readily synthesized, via rearrangement reactions between Lewis acidic B(C6F5)(3) and propargyl esters. These reactions proceed through an initial cyclization followed by ring-opening and concurrent C6F5-group migration. In the absence of disubstitution adjacent to the ester oxygen atom, an allyl boron migration rearrangement leads to formal 1,3-carboboration products. These allyl boron compounds act as allylation reagents with aldehydes introducing both a C-3-allyl fragment and a C6F5-unit as a single anti-diastereomer. In these reactions, (C6F5)(3) activates the alkynes, prompting the rearrangement processes and enabling installations of C6F5 and R-groups.
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