S. Yuan, A. Ajami
Mar 18, 1986
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0
Influential Citations
4
Citations
Journal
Journal of Organometallic Chemistry
Abstract
Abstract Substituted allylic alcohols (3-methyl-2-buten-1-ol and 2-methyl-3-buten-2-ol) were isomerized and amidocarbonylated. In addition to the expected product, N -acetylleucine, arising from their rearrangement to 3-methylbutanal and subsequent amidocarbonylation (22% yield), we isolated two additional products (28% yield). These were shown by spectroscopic methods and by syntheses, via amidocarbonylations of the respective aldehydes, to be 2-acetamido-5-methylhexanoic acid and 2-acetamido-4-methylhexanoic acid. Their formation is postulated to be the sequential result of (i) dehydration first to form isoprene, (ii) hydroformylation and hydrogenation of isoprene to give 3-methyl-1-pentanal and 4-methyl-1-pentanal, and (iii) aldehyde amidocarbonylation. Treatment of isoprene itself under the same conditions also gave these latter two acetylamino acids.