Journal
ORGANIC LETTERS
Volume 11, Issue 5, Pages 1059-1061Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol802781c
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Funding
- National Institutes of Health [GM067146]
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Treatment of 2-(2'-alkenyl)-piperidine boranes with iodine or triflic acid induces internal hydroboration with high regiocontrol, even with a terminal alkene (R = H). Good stereocontrol is possible for the N-benzyl substrates. Comparisons with acyclic model structures show that the source of regiocontrol with the terminal alkene is due to a steric effect of the axial piperidine C(3,5) hydrogens that destabilize the competing bridged bicyclic transition state.
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