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Synthesis of Amines from Alcohols in a Nonepimerizing One‐Pot Sequence – Synthesis of Bioactive Compounds: Cinacalcet and Dexoxadrol
Author(s) -
Guérin Claire,
Bellosta Véronique,
Guillamot Gérard,
Cossy Janine
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200171
Subject(s) - chemistry , iminium , alkylation , cinacalcet , organic chemistry , imine , epimer , nucleophile , sequence (biology) , combinatorial chemistry , one pot synthesis , nucleophilic addition , nucleophilic substitution , catalysis , parathyroid hormone , biochemistry , secondary hyperparathyroidism , calcium
A general, mild, and chemoselective one‐pot oxidation/imine‐iminium formation/nucleophilic addition sequence allowing the N ‐alkylation of amines by alcohols is described. This metal‐free, one‐pot sequence produced a wide variety of amines in good yields and diastereoselectivities, without the epimerization of the enantioenriched amines or alcohols involved in the process. This method was applied to the syntheses of the biologically active compounds cinacalcet and dexoxadrol.