Abstract
The Candida antarctica lipase catalyzed esterification of the hydroxymethyl sulfones rac- 1a and rac- 1b led to the isolation of ent- 1a (92% ee) and 1b (≥99% ee), respectively. The acyloxymethyl sulfone ent- 7a (≥99% ee) was obtained by the Candida antarctica lipase catalyzed hydrolysis of rac- 7a . Not only Candida antarctica lipase but also Pseudomonas cepacia lipase showed the opposite enantiomer differentiation in the esterification of the methyl substituted alcohol rac- 1a and the benzyl substituted alcohol rac- 1b . The absolute configuration of ent- 1a and 1b was determined by measurement of their circular dichroism and the calculation of the CD spectra of 1a and 1b by semiempirical methods. The configurational assignment was verified by X-ray structure analysis of 1b and ent- 7a .
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