Fleming, Fraser F.; Wei, Guoqing; Steward, Omar W. published the artcile< Cyclic Nitriles: Stereodivergent Addition-Alkylation-Cyclization to cis- and trans-Abietanes>, Electric Literature of 16799-05-6, the main research area is stereoselective synthesis abietane diterpene addition alkylation cyclization cyclic nitrile; Friedel Crafts cyclization stereoselective synthesis abietane diterpene.
Diverse cyclic hydroxy nitriles are readily synthesized through sequential 1,2-1,4-Grignard addition-methylations to 3-oxo-1-cyclohexene-1-carbonitrile. Acid-catalyzed intramol. cyclizations of the cyclic hydroxy nitriles reveal fundamental stereoselectivity trends in Friedel-Crafts cyclizations to cis- and trans-abietanes, e.g. I and II. In contrast to previous assumptions, comparative cationic cyclizations with electron-rich and electron-poor aromatic nucleophiles exhibit similar preferences for cyclization to cis-abietanes. Optimizing the cyclizations for trans-abietanes has identified ZrCl4 as an exceptional Lewis acid which, for cyclizations of iminolactones, favors trans-abietanes as the only observable diastereomer. The sequential oxonitrile addition-Friedel-Crafts cyclization strategy provides a rapid, stereodivergent synthesis of cis- or trans-abietanes, demonstrates the dramatic influence of ZrCl4 in promoting cationic cyclizations, and in contrast to previous assumptions suggests that the cyclization stereoselectivity is not correlated with the electronic nature of the aromatic nucleus.
Journal of Organic Chemistry published new progress about Abietanes Role: SPN (Synthetic Preparation), PREP (Preparation). 16799-05-6 belongs to class chlorides-buliding-blocks, and the molecular formula is C8H8BrCl, Electric Literature of 16799-05-6.
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics