TY - JOUR
T1 - Uncatalyzed Carboboration of Seven-Membered-Ring trans-Alkenes
T2 - Formation of Air-Stable Trialkylboranes
AU - Sanzone, Jillian R.
AU - Hu, Chunhua T.
AU - Woerpel, K. A.
PY - 2017/6/28
Y1 - 2017/6/28
N2 - Seven-membered-ring trans-alkenes undergo rapid, uncatalyzed carboboration reactions to form trialkylboranes as single diastereomers. In contrast with other trialkylboranes, which can ignite in the presence of oxygen, these trialkylboranes are stable in air. Hindered trialkylboranes can undergo reverse hydroboration reactions to form allylic silanes or can be oxidized to afford highly substituted triols. This reaction sequence permits the construction of compounds with up to five consecutive stereocenters. Control experiments and computational studies support a concerted mechanism for the migratory insertion of the alkene into the carbon-boron bond, similar to the mechanism for hydroboration.
AB - Seven-membered-ring trans-alkenes undergo rapid, uncatalyzed carboboration reactions to form trialkylboranes as single diastereomers. In contrast with other trialkylboranes, which can ignite in the presence of oxygen, these trialkylboranes are stable in air. Hindered trialkylboranes can undergo reverse hydroboration reactions to form allylic silanes or can be oxidized to afford highly substituted triols. This reaction sequence permits the construction of compounds with up to five consecutive stereocenters. Control experiments and computational studies support a concerted mechanism for the migratory insertion of the alkene into the carbon-boron bond, similar to the mechanism for hydroboration.
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U2 - 10.1021/jacs.7b03986
DO - 10.1021/jacs.7b03986
M3 - Article
C2 - 28565903
AN - SCOPUS:85021670183
VL - 139
SP - 8404
EP - 8407
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 25
ER -