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Asymmetric synthesis of (R,S)- and (R,R)-4-hydroxy-5-(α-substituted)-hydroxymethyl[2.2]paracyclophane and derivatives by stereoselective addition to (R)-4-hydroxy-5-formyl[2.2]paracyclophane and derivatives

✍ Scribed by Elena V Sergeeva; Valeria I Rozenberg; Evgenii V Vorontsov; Tat'yana I Danilova; Zoya A Starikova; Alexandr I Yanovsky; Yuri N Belokon'; Henning Hopf

Publisher: Elsevier Science
Year: 1996
Tongue: English
Weight: 548 KB
Volume: 7
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(96)00452-1

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✦ Synopsis

Highly diastereoselective nucleophilic addition reactions of organometallic reagents to formyl[2.2]paracyclophane derivatives which were ortho-substituted by hydroxy-, alkoxy-and trimethylsilyloxy-groups are reported. The absolute configuration of the newly formed secondary alcohols is assigned on the basis of the X-ray diffraction study as well as chemical correlation. The magnitude of the asymmetric induction and even the sense of chirality of the forming asymmetric carbon atoms of the alcohols depended on the nature of the orthosubstituents.

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