Can this alcohol be synthesized selectively by hydroboration-oxidation of an alkene?.

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02-11-2022
Biology

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Can this alcohol be synthesized selectively by hydroboration-oxidation of an alkene?.

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fawadmohd fawadmohd · Answer 1 · 2022-11-06T01:08:04-04:00

yes this alcohol be synthesized selectively by hydroboration-oxidation of an alkene.

The initial hydroboration step determines the regioselectivity. Hydroboration proceeds in an antimarkovnikov manner. The reaction sequence is also stereoselective, giving syn addition (on the same face of the alkene): the hydroboration is syn-selective and the oxidation replaces the boron with hydroxyl having the same geometric position.

Thus 1-methyhexene reacts with diborane predominantly to give trans-1-hydroxy-2-methylhexene and the newly added H and OH are cis to each other.

CH3-CH2-CH2-CH2-C(CH3)=CH2

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