ChemInform Abstract: Asymmetric Dihydroxylation of 1-Acyloxy-2(E)-alkenylphosphonates with AD-mix Reagents. Effects of 1-Acyloxy Functional Groups on the Asymmetric Dihydroxylation.

✍ Scribed by T. YOKOMATSU; T. YAMAGISHI; T. SADA; K. SUEMUNE; S. SHIBUYA

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 38 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199821031

✦ Synopsis

Asymmetric Dihydroxylation of 1-Acyloxy-2(E)-alkenylphosphonates with AD-mix Reagents. Effects of 1-Acyloxy Functional Groups on the Asymmetric Dihydroxylation. -The reaction of a racemic mixture of the title phosphonates with an AD-mix-β reagent preferentially dihydroxylates the (R)-enantiomer to leave the unreacted (S)-enantiomer of high enantiomeric purity.

The dihydroxylation of the optically active (R)-(Ib) enantiomer, resolved with the AD-mix-α reagent, provides polyoxygenated phosphonate (V) with high diastereoselectivity. -(YOKOMATSU, T.; YAMAGISHI, T.;