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Synthesis of Amines and Amino Alcohols by Electrophilic Amination and Highly Stereoselective Reduction
Author(s) -
Gmeiner Peter,
Bollinger Bernd
Publication year - 1992
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.199219920147
Subject(s) - chemistry , stereoselectivity , steric effects , electrophilic amination , electrophile , amination , reductive amination , cis–trans isomerism , stereochemistry , organic chemistry , catalysis
A practical and selective method for the synthesis of the β‐arylamines 5 and the cis ‐ or trans ‐amino alcohols 8 or 11 is reported. The reaction sequence starts from α‐tetralones 1 which readily react with dibenzyl azodicarboxylate to afford the protected α‐hydrazino ketones 2 . Then, depending on the reduction conditions , the trans ‐hydrazino alcohols 10 or the cis isomers 7 are formed predominantly. The stereoselectivities which range between 18:1 and 1:67 ( trans/cis ) are explained by stereoelectronic effects (σ,σ ≠ *interactions) and steric hindrance. Depending on the workup procedure , we can control, whether the cis ‐hydrazino alcohols 7 or the oxazolidinone derivatives 3 are isolated. Subsequent hydrogenolyses of 4, 7 and 10 lead to the target molecules 5, 8 and 11 , respectively.