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Regio‐ and Diastereoselective Three‐Component Syntheses of Homoallylic Amines in Aqueous Media Catalyzed by Brønsted Acids
Author(s) -
Deng DongSheng,
Liu Ping,
Cai Jiwen
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600944
Subject(s) - chemistry , regioselectivity , reagent , catalysis , aqueous medium , brønsted–lowry acid–base theory , organic chemistry , aqueous solution , combinatorial chemistry
A systematic investigation into the three component allylation reaction of aldehydes, amines, and allyltributylstannanes catalyzed by Brønsted acids in aqueous media was reported. The reaction was effective and able to produce homoallylic amines in moderate to high yields under mild conditions, with a good scope of substrates. Moreover, the regioselectivity of the reaction favors the formation of the γ‐product, and good diastereoselectivity in favor of the syn isomers when cinnamyltributylstannane was employed as the allylation reagent was observed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)