ChemInform Abstract: A Valuable Synthetic Route to Spiro-Cyclopropane Derivatives Containing Multiple Stereogenic Centers.

✍ Scribed by Hui Huang; Qinghua Chen

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 35 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199939080

✦ Synopsis

A Valuable Synthetic Route to Spiro-Cyclopropane Derivatives Containing Multiple Stereogenic Centers.

-Tandem double Michael addition-intramolecular nucleophilic substitution reaction of a novel chiral synthon (II) with various oxygen nucleophiles (III) and (V) provides the title spiro-cyclopropane derivatives (IV) and (VI), resp., containing at least four stereogenic centers, in excellent diastereoselectivity (≥ 98% d.e.). Interestingly, analogous reaction of compound (II) with ethyl chloro-or bromoacetate (VII) furnishes the O-CH 2 linked (VIII) rather than the expected C-C linked acetate.

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