期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 66, 期 24, 页码 8120-8126出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo015950x
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The reaction of acetylated a-allenic alcohols with LiBr in the presence of 1.5 mol % of Pd(OAc)(2) provides easy access to substituted (Z,E)-2-bromo-1,3-dienes in good yields with excellent diastereoselectivity. Both secondary and tertiary acetates as well as terminal and nonterminal allenes were studied to investigate the scope and the limitations of the reaction. A mechanism is proposed to clarify how a diastereomeric mixture of the starting compound is transformed into a single diastereomer of the product.
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