ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACID DERIVATIVES VIA AN ELECTROPHILIC AMINATION OF CHIRAL AMIDE CUPRATES WITH LI T-BUTYL-N-TOSYLOXYCARBAMATE

Authors
ZHENG N ARMSTRONG JD MCWILLIAMS JC VOLANTE RP
Citation
N. Zheng et al., ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACID DERIVATIVES VIA AN ELECTROPHILIC AMINATION OF CHIRAL AMIDE CUPRATES WITH LI T-BUTYL-N-TOSYLOXYCARBAMATE, Tetrahedron letters, 38(16), 1997, pp. 2817-2820
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
16
Year of publication
1997
Pages
2817 - 2820
Database
ISI
SICI code
0040-4039(1997)38:16<2817:AOADVA>2.0.ZU;2-F
Abstract
The utility of lithium t-butyl-N-tosyloxycarbamate (LiBTOC) as a (+)NH BOC synthon in highly diastereoselective reactions with chiral cis-ami noindanol derived amide cuprates is described. The diastereoselectivit ies of these reactions ranged from 96% to greater than 99%. The subseq uent transformation of these adducts to alpha-amino acids ir also desc ribed (C) 1997 Elsevier Science Ltd.