The stereochemistry of hydroboration of conjugated ketones
1968; Elsevier BV; Volume: 24; Issue: 16 Linguagem: Inglês
10.1016/0040-4020(68)88168-2
ISSN1464-5416
Autores Tópico(s)Chemical Synthesis and Analysis
ResumoThe hydroboration of isophorone (I) and 3-methylcyclohexenone (II) yielded single diols, which were shown to be the diequatorial isomers (X and XIII) by chemical and physical methods. The same reaction with piperitone (III) yielded two diols (XV and XVI) both with hydroxyls in diequatorial positions. A small fraction of monoalcohols was also obtained. The mechanism of these reactions is discussed. The open chain analog IV did not show stereospecificity during hydroboration.
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