Dihydroxycyclohexyl acetonitrile acetonide

2-Dihydroxycyclohexyl)acetonitrile (2.1 g) was placed in a lOOmL round-bottomed flask equipped with a magnetic stirrer bar. Dry tetrahydrofuran (40 mL) was added followed by CSA (0.04 g) and 2-methoxypropene (2.5 mL). The solution was stirred at room temperature for 90 minutes. 

The reaction was monitored by TLC (eluent petroleum ether-ether, 1 2). Diol and acetonide spots, visualized by /i-anisaldehyde dip, have Rf values of 0 and 0.35 respectively. 

The reaction mixture was concentrated using a rotary evaporator. The residue was chromatographed on silica gel (eluent ether-petroleum ether, 1 3) to afford a white solid (97 %). 

The absolute configuration was determined by chemical correlation with the known (2R)-2-allyl-2-hydroxycyclohexanone. 

Sharpless asymmetric dihydroxylation has been successfully applied to (1-cyclopentenyl)acetonitrile. Using (DHQ)PHN as a ligand in place of (DHQ)2PHAL, one of the components of AD-mix-a, (A, A)-(l, 2-dihydroxycy-clopentyl)acetonitrile was obtained after two recrystallizations, in 50% yield 

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