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Stereoselective synthesis of β-hydroxycyclohexanones

✍ Scribed by Alistair P. Rutherford; Cameron S. Gibb; Richard C. Hartley

Book ID: 104258553
Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 220 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)10635-9

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✦ Synopsis

We have developed a stereoselective route to 13-hydroxycyclohexanones using the aldol reaction, the Takai alkylidenation, a novel anionic oxy-Cope rearrangement of acyclic enol ethers and an intramolecular aldol reaction. The stereoselectivity of the acid-induced, 6-(enolendo)-exo-trig, intramolecular, aldol reaction between an aldehyde and an enol ether has been investigated. The strong preference for an axial hydroxyl in the 13-hydroxycyclohexanone products is explained in terms of an electrostatic interaction in the oxonium ion intermediate.

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