Alkylmetal Asymmetric Reduction. 18. Starting Materials in the Preparation of New Chiral Reducing Agents: Synthetic Approach to Primary Alkyl Halides Derived from (+)-Camphor

Article abstract of DOI:10.1021/jo00376a045

2,2-Dimethyl-3-(chloromethyl)bicyclo<2.2.1>heptane (camphanyl chloride), camphanyl bromide, 1,7,7-trimethyl-2-(chloromethyl)bicyclo<2.2.1>heptane <2-(chloromethyl)bornane>, and 2-(bromomethyl)bornane were prepared from (+)-camphor.All these compounds were obtained as mixture of exo and endo isomers in various ratios depending upon the synthetic path adopted.A loss of diastereomeric purity during the halogenations of corresponding alcohols was observed.