ChemInform Abstract: Catalytic Asymmetric Synthesis of syn-Aldol Products from Intermolecular C—H Insertions Between Allyl Silyl Ethers and Methyl Aryldiazoacetates.

✍ Scribed by Huw M. L. Davies; Evan G. Antoulinakis; Tore Hansen

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 32 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199946093

✦ Synopsis

Catalytic Asymmetric Synthesis of syn-Aldol Products from Intermolecular C-H Insertions Between Allyl Silyl Ethers and Methyl Aryldiazoacetates.

-The simple allyloxy derivative (I) undergoes a Rh-catalyzed reaction with 4-chlorophenyldiazoacetate (II) to give the cyclopropane (III). The allyl silyl ether (IV) gives a mixture of cyclopropanation and C-H insertion products (V) and (VI). Repeating the reaction with more highly substituted allyl ethers gives only C-H insertion products [cf. (VIII) and (X)].