Premium
Utilization of Industrial Waste Materials, 11. Synthesis of New, Chiral β‐ sec ‐Amino Alcohols – Diastereodivergent Addition of Grignard Reagents to α‐Amino Aldehydes Based on the ( all ‐ R )‐2‐Azabicyclo[3.3.0]octane System
Author(s) -
Wilken Jörg,
Thorey Claire,
Gröger Harald,
Haase Detlev,
Saak Wolfgang,
Pohl Siegfried,
Muzart Jacques,
Martens Jürgen
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719971016
Subject(s) - diastereomer , chemistry , reagent , homogeneous , amine gas treating , alcohol , catalysis , organic chemistry , chelation , grignard reaction , combinatorial chemistry , stereochemistry , physics , thermodynamics
Abstract New, chiral β‐ sec ‐amino alcohols (α R ,β R )‐ 11a – 13a , (α S ,β R )‐ 11b–17b , (α S ,β S )‐ 11c, 12c, 15c, 17c and (α R ,β S )‐ 11d, 12d, 15d, 17d have been synthesized from the enantiomerically pure amine ( all‐R )‐ 1a via diastereomeric, N‐tert ‐butoxycarbonyl‐protected aldehydes 3 . Grignard additions proceed in fair yields with a high degree of diastereofacial stereoselection (diastereomeric ratios dr up to ⩾ 95:5) with non‐chelation control, generally in favor of the anti‐(erythro) structures. A mechanistic interpretation of the stereochemical course of this reaction is presented. The stereodifferentiating ability of selected stereoisomeric ( erythro )‐ and ( threo )‐amino alcohol structures were tested in homogeneous catalysis, e.g. in two model reactions (optical purities up to 95%).