FIRST ENANTIOSELECTIVE SYNTHESIS OF A 1-(TRIMETHYLSILYL)ALKYLAMINE

Authors
PICARD JP FORTIS F
Citation
Jp. Picard et F. Fortis, FIRST ENANTIOSELECTIVE SYNTHESIS OF A 1-(TRIMETHYLSILYL)ALKYLAMINE, Tetrahedron : asymmetry, 9(19), 1998, pp. 3455-3460
Citations number
35
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
19
Year of publication
1998
Pages
3455 - 3460
Database
ISI
SICI code
0957-4166(1998)9:19<3455:FESOA1>2.0.ZU;2-C
Abstract
Reduction of n-propanoyrtrimethylsilane NH-imine with the complex hydr ide LiBH4/diethyltartrate in THF yielding enantiomerically enriched 1- (trimethylsilyl)butylamine with a 60% enantiomeric excess is the first example of the enantioselective synthesis of such an amine. Other com binations of solvent (ether or THF), hydride (NaBH4 or LiAlH4) and chi ral inductor (mono- or diol) failed. (C) 1998 Elsevier Science Ltd, Al l rights reserved.