UTILIZATION OF INDUSTRIAL-WASTE MATERIALS .11. SYNTHESIS OF NEW, CHIRAL BETA-SEC-AMINO ALCOHOLS - DIASTEREODIVERGENT ADDITION OF GRIGNARD-REAGENTS TO ALPHA-AMINO ALDEHYDES BASED ON THE (ALL-R)-2-AZABICYCLO[3.3.0]OCTANE SYSTEM

New, chiral beta-sec-amino alcohols (alpha R,beta R)-11a-13a, (alpha S ,beta R)- 11b-17b, (alpha S,beta S)-11c, 12c, 15c, 17c and (alpha R,be ta S)-11d, 12d, 15d, 17d have been synthesized from the enantiomerical ly pure amine (all-R)-1a via diastereomeric, N-tert-butoxycarbonyl-pro tected aldehydes 3. Grignard additions proceed in fair yields with a h igh degree of diastereofacial stereoselection (diastereomeric ratios d r up to greater than or equal to 95:5) with non-chelation control, gen erally in favor of the anti-(erythro) structures. A mechanistic interp retation of the stereochemical course of this reaction is presented. T he stereodifferentiating ability of selected stereoisomeric (erythro)- and (threo)-amino alcohol structures were tested in homogeneous catal ysis, e.g. in two model reactions (optical purities up to 95%).