Brønsted Acid-Catalyzed, Enantioselective, Vinylogous Mannich Reaction of Vinylketene Silyl N,O-Acetals

Autor:	Christoph Schneider, David S. Giera, Marcel Sickert
Rok vydání:	2008
Předmět:	Silylation Chemistry Organic Chemistry Enantioselective synthesis Organic chemistry Physical and Theoretical Chemistry Brønsted–Lowry acid–base theory Biochemistry Mannich reaction Catalysis
Zdroj:	Organic Letters. 10:4259-4262
ISSN:	1523-7052 1523-7060
DOI:	10.1021/ol8017374
Popis:	Vinylketene silyl N, O-acetals undergo chiral phosphoric acid-catalyzed, vinylogous Mukaiyama-Mannich reactions with imines and afford delta-amino-alpha,beta-unsaturated amides in typically good yields, complete gamma-regioselectivity, and up to 92% ee with catalyst loadings of as low as 1 mol %. The Mannich products can be readily manipulated to furnish valuable synthetic intermediates.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::c56778a2d2f7835e8000741a679952f8 https://doi.org/10.1021/ol8017374 Zobrazit plný text záznamu