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One‐Pot Addition/Reduction Procedure for the Synthesis of ‐Amino Alcohols from ‐Enamino Ketones
Author(s) -
Cimarelli Cristina,
Giuli Sandra,
Palmieri Gianni
Publication year - 2006
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.200500702
Subject(s) - chemistry , reagent , stereoselectivity , carbon atom , organic chemistry , carbon fibers , nuclear magnetic resonance spectroscopy , combinatorial chemistry , catalysis , alkyl , materials science , composite number , composite material
γ‐Amino alcohols 3 have been synthesized by the addition of organolithium reagents to β‐enamino ketones 1 followed by one‐pot reduction with sodium triacetoxyborohydride. The method allows the stereoselective synthesis of γ‐amino alcohols in which the hydroxy group is bonded to a fully substituted carbon atom. The relative configuration of the chiral product was determined by 1 H NMR spectroscopy. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)