ChemInform Abstract: Diastereoselective Uncatalyzed Conjugate Addition of Organoaluminum Reagents: Efficient Desymmetrization of (R)-((p-Tolylsulfinyl)methyl) quinols.

✍ Scribed by M. C. CARRENO; M. PEREZ GONZALEZ; M. RIBAGORDA; J. FISCHER

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 32 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199705062

✦ Synopsis

Diastereoselective Uncatalyzed Conjugate Addition of Organoaluminum Reagents:

Efficient Desymmetrization of (R)-((p-Tolylsulfinyl)methyl) quinols.

-The exclusive 1,4-addition of organoaluminum reagents to (I) and (IV) proceeds without metal catalysts under mild conditions with good yields. The generation of only one of the four possible diastereomers is established by 1H NMR and X-ray structures. The lack of 1,4-addition if a methyl-protected p-quinol (I) reacts with (Vb) indicates that the free OH group is necessary to assist the organoaluminum reagent in the transfer of the organic residue. A reaction mechanism is proposed. -(CARRENO, M. C.;