Diastereoselective synthesis of enantiopure gamma-amino-beta-hydroxy acidsby Reformatsky reaction of chiral alpha-dibenzylamino aldehydes

Authors
Andres, JM Pedrosa, R Perez, A Perez-Encabo, A
Citation
Jm. Andres et al., Diastereoselective synthesis of enantiopure gamma-amino-beta-hydroxy acidsby Reformatsky reaction of chiral alpha-dibenzylamino aldehydes, TETRAHEDRON, 57(40), 2001, pp. 8521-8530
Citations number
43
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
40
Year of publication
2001
Pages
8521 - 8530
Database
ISI
SICI code
0040-4020(20011001)57:40<8521:DSOEGA>2.0.ZU;2-K
Abstract
N,N-Dibenzylamino aldehydes 1 react with Reformatsky's reagent leading to a nti-gamma -dibenzylamino-beta -hydroxy esters 2 as the major stereoisomers. Treatment of 2 with TFA followed by hydrogenolysis on Pearlman's catalyst yields the corresponding-gamma -amino-beta -hydroxy acids 10. Contrarily, s ome N-butoxycarbonyl (Boc) amino aldehydes lead to syn-gamma -tert-butoxyca rbonylamino-beta -hydroxy esters as the major product. (C) 2001 Elsevier Sc ience Ltd. All rights reserved.