ChemInform Abstract: A Stereoselective, Tandem [2 + 2] Photocycloaddition—Hydrolysis Route to Aldol-Type Adducts.

✍ Scribed by M. ABE; M. IKEDA; M. NOJIMA

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 32 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199909122

✦ Synopsis

A Stereoselective, Tandem [2 + 2] Photocycloaddition-Hydrolysis Route to Aldol-Type Adducts.

-The photocycloaddition of aromatic aldehydes (I) with cyclic ketene silyl acetals (II) or (V) proceeds regio-and stereoselectively to afford predominantly bicyclic oxetanes [cf. (III)] having exo-configuration. Hydrolysis of the acid-labile oxetanofurans provides access to aldol-type adducts [cf. (IV), (VI)/(VII)] with no loss of stereochemistry. -