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On the Diastereoselectivity of the Aqueous-Acid-Catalyzed Intramolecular Aldol Condensation of 3-Oxocyclohexaneacetaldehydes

✍ Scribed by Barbara De Santis; Anna Laura Iamiceli; Rinaldo Marini Bettolo; Luisa Maria Migneco; Rita Scarpelli; Giorgio Cerichelli; Giancarlo Fabrizi; Doriano Lamba

Publisher: John Wiley and Sons
Year: 1998
Tongue: German
Weight: 255 KB
Volume: 81
Category: Article
ISSN: 0018-019X
DOI: 10.1002/(sici)1522-2675(19981216)81:12<2375::aid-hlca2375>3.0.co;2-0

No coin nor oath required. For personal study only.

✦ Synopsis

Dedicated to the memory of Prof. Giacomino Randazzo

The factors responsible for the diastereoselective formation of the 6-endo-hydroxybicyclo[2.2.2]octan-2one by acid-catalyzed intramolecular aldol reaction of 3-oxocyclohexaneacetaldehydes have been investigated. This study, carried out on (1SR,4RS,6RS)-6-hydroxybicyclo[2.2.2]octan-2-one 1a, (1SR,4RS,6SR)-6-hydroxybicyclo[2.2.2]octan-2-one 1b, and 3,3-(ethylenedioxy)cyclohexaneacetaldehyde 2a, allowed to demonstrate the absence of intramolecular H-bonding in 1a as a stabilizing factor, and to ascertain the presence of unfavorable steric interactions in 1b.

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