hydroxycyclization

English

Etymology

hydroxy +‎ cyclization

Noun

hydroxycyclization (plural hydroxycyclizations)

  1. (organic chemistry) A reaction in which the addition of a hydroxy group to one carbon atom of a double or triple bond is accompanied by cyclization
    • 2015 June 10, Ruth Dorel, Antonio M. Echavarren, “Gold-Catalyzed Reactions via Cyclopropyl Gold Carbene-like Intermediates”, in The Journal of Organic Chemistry‎, volume 80, →DOI:
      A transition state similar to TS 34 – 33 has been proposed in the reaction of cyclopropyl gold(I) carbenes generated by retro-Buchner reaction of 7-cyclopropyl 1,3,5-cycloheptatrienes. 79 Gold(I) complexes are able to catalyze the addition of amines, alcohols, or water to 1, n -enynes affording products of amino-, alkoxy-, or hydroxycyclization under much milder conditions than other metal catalysts. 26, 32, 33, 62, 80 − 82 These additions are stereospecific, as illustrated by the alkoxycyclization of diastereomeric enynes 1m and 1h, and proceed via opening of cyclopropyl gold(I) carbene intermediates 35 by attack of the nucleophile to the cyclopropane ring (Scheme 11 ).
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