Nucleophilic addition to an achiral dehydroalanine Schiff base Ni(II) complex as a route to amino acids. A case of stereodetermining asymmetric protonation in the presence of TADDOL

Autor:	Albert K. Beck, Dieter Seebach, Ashot S. Sagyan, E. V. Vorontsov, Yuri N. Belokon, Dmitriy A. Pripadchev, Konstantin A. Kochetkov, Viktor N. Chrustalev, Syuzanna R. Harutyunyan, Alexander S. Peregudov
Přispěvatelé:	Stratingh Institute of Chemistry
Rok vydání:	2004
Předmět:	Schiff base Nucleophilic addition Stereochemistry Organic Chemistry Enantioselective synthesis Protonation Catalysis lcsh:QD241-441 TADDOL chemistry.chemical_compound lcsh:Organic chemistry chemistry Nucleophile Dehydroalanine Michael addition Michael reaction asymmetric protonation amino acid
Zdroj:	Arkivoc, 2004(3), 132-150. ARKAT USA INC ARKIVOC, Vol 2004, Iss 3, Pp 132-150 (2004)
ISSN:	1551-7012 1424-6376
DOI:	10.3998/ark.5550190.0005.313
Popis:	We describe herein the elaboration of a new type of a substrate based on the Ni(II) complex of a Schiff base of dehydroalanine, 1, and Michael addition of nucleophiles to it, leading to the synthesis of racemic α-amino acids. We have also developed a catalytic method for the asymmetric 1,4 conjugate addition of achiral CH-acids to 1 promoted by TADDOLs with enantioselective catalytic protonation of the intermediate enolate in the stereodetermining stage of the reaction. A sizable 80% ee of the product was observed.
Databáze:	OpenAIRE
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