The hydroboration of 3α-, 3β-, 6α- and 6β-methoxyandrost-4-enes has been shown to proceed predominantly trans to the methoxy group with, in the case of the 6-methoxy compounds, some Markownikoff hydration to form the tertiary C-5 alcohols, thus parallelling results obtained with the corresponding alcohols.
J. R. Hanson and S. Nagaratnam, J. Chem. Res. (S), 1998, 540 DOI: 10.1039/A802860E
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