title: Proline-catalyzed asymmetric aldol reactions between ketones and alpha-unsubstituted aldehydes.
abstract: [reaction: see text] With this communication we extend the methodology of proline-catalyzed direct asymmetric aldol reactions to include alpha-unsubstituted aldehydes as acceptors. This important aldehyde class gives the corresponding aldols in 22-77% yield and up to 95% ee when the reactions are performed in pure acetone or in ketone/chloroform mixtures. On the basis of these results we have developed a concise new synthesis of (S)-ipsenol.
authors.affiliation: Departments of Chemistry and Molecular Biology, The Scripps Research Institute, La Jolla, California 92037, USA. blist@scripps.edu
authors.forename: B
authors.initials: B
authors.lastname: List
authors.forename: P
authors.initials: P
authors.lastname: Pojarliev
authors.forename: C
authors.initials: C
authors.lastname: Castello
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000447:Aldehydes; D007659:Ketones; C424142:ipsenol; D011392:Proline