Abstract
Repetitive asymmetric aldol reactions between bis(trimethylsilyl thioketene acetal) 2 and dialdehyde (3, 4) proceeded smoothly in the presence of enantiopure N-tosyl oxazaborolidinone 1 as a chiral Lewis acid catalyst. Optically active poly(β-hydroxy thioester)s (10, 11) having main-chain configurational chirality were obtained by the asymmetric aldol polymerization. Precise model reaction studies supported the idea that asymmetric aldol polymerization should occur in a stereoselective manner. Degradation of the optically active polymers followed by chiral HPLC analysis of the degraded products was found to be a useful method to estimate the optical purity of the polymers.
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