Lipase catalyzed resolution of α-hydroxymethyl sulfones. Determination of absolute configuration by semiempirical calculation of CD spectra and verification by X-ray structure analysis

Article abstract of DOI:10.1016/S0957-4166(97)00377-7

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% eel, 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.