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Verwertung industrieller Abfallstoffe, 4. Synthese neuer, chiraler β‐Aminoalkohole und deren Anwendung in der katalytischen enantioselektiven Addition von Diethylzink an Benzaldehyd
Author(s) -
Stingl Klaus,
Martens Jürgen
Publication year - 1994
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.15619940508
Subject(s) - diethylzinc , benzaldehyde , enantioselective synthesis , chemistry , stereocenter , aldehyde , catalysis , organic chemistry , reagent
Utilization of Industrial Waste Materials, 4. – Synthesis of New, Chiral β‐Amino Alcohols and Their Applications in the Catalytic Enantioselective Addition of Diethylzinc to Benzaldehyde This report describes the synthesis of new, chiral β‐amino alcohols 4a–g with four stereogenic centers. Thus, Grignard reagents are added diastereoselectively to an α‐amino aldehyde. Selected chiral amino alcohols 4a–g and the corresponding lithium alkoxides were used in the catalytic enantioselective addition of diethylzinc to benzaldehyde. 1‐Phenylpropan‐1‐ol was obtained in up to 86% ee. This is another example for the synthesis of interesting chiral ligands from the industrial waste material ( all‐R )‐ 1a .