Catalysis of 3-Pyrrolidinecarboxylic Acid and Related Pyrrolidine Derivatives in Enantioselective anti-Mannich-Type Reactions: Importance of the 3-Acid Group on Pyrrolidine for Stereocontrol

Autor:	Carlos F. Barbas, Naoto Utsumi, Fujie Tanaka, Haile Zhang, Paul Ha-Yeon Cheong, Klaus Albertshofer, Susumu Mitsumori, Maria Mifsud, Masanori Imai, Kendall N. Houk, Noemi Garcia-Delgado
Rok vydání:	2007
Předmět:	3-pyrrolidinecarboxylic acid Enantioselective synthesis General Chemistry Bond formation Ring (chemistry) Biochemistry Catalysis Pyrrolidine chemistry.chemical_compound Colloid and Surface Chemistry chemistry Organic chemistry heterocyclic compounds Acid group Efficient catalyst
Zdroj:	Journal of the American Chemical Society. 130:875-886
ISSN:	1520-5126 0002-7863
DOI:	10.1021/ja074907+
Popis:	The development of enantioselective anti-selective Mannich-type reactions of aldehydes and ketones with imines catalyzed by 3-pyrrolidinecarboxylic acid and related pyrrolidine derivatives is reported in detail. Both (3R,5R)-5-methyl-3-pyrrolidinecarboxylic acid and (R)-3-pyrrolidinecarboxylic acid efficiently catalyzed the reactions of aldehydes with α-imino esters under mild conditions and afforded anti-Mannich products with high diastereo- and enantioselectivities (anti/syn up to 99:1, up to >99% ee). For the reactions of ketones with α-imino esters, (R)-3-pyrrolidinecarboxylic acid was an efficient catalyst (anti/syn up to >99:1, up to 99% ee). Evaluation of a series of pyrrolidine-based catalysts indicated that the acid group at the β-position of the pyrrolidine ring of the catalyst played an important role in forwarding the carbon−carbon bond formation and in directing anti-selectivity and enantioselectivity.
Databáze:	OpenAIRE
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