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• W2150513302 abstract "Synthesis of camphor derived chiral allenes and their hydroboration-oxidation reactions are described. Reaction of (1R)-(+)-camphor with alkynyllithium followed by the reduction of the resulted propargyl alcohol derivatives using AlH3 furnished chiral allenes 2a-g in excellent yields with high diastereoselectivity. Reduction of the propargyl alcohols with aluminum hydride proceeded through selective intermolecular anti-addition of hydride ion. The stereochemistry of the chiral allenes 2 was assigned based on lanthanide shift studies and chemical correlations. Diastereoselectivity was observed in the hydroboration-oxidation of 2 which produced a mixture of (E,R) and (E,S) stereoisomers in a ratio of 6:1 to 18:1." @default.
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• W2150513302 date "2002-01-25" @default.
• W2150513302 modified "2023-10-16" @default.
• W2150513302 title "A Highly Diastereoselective Synthesis of (1<i>R</i>)-(+)-Camphor-Based Chiral Allenes and Their Asymmetric Hydroboration−Oxidation Reactions" @default.
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• W2150513302 doi "https://doi.org/10.1021/jo016201i" @default.
• W2150513302 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/11846679" @default.
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