4.7 Article

Chemo- and Enantioselective Bronsted Acid-Catalyzed Reduction of α-Imino Esters with Catecholborane

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 355, Issue 10, Pages 1937-1942

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201300352

Keywords

amino acids; BrOnsted acids; catecholborane; organocatalysis; phosphoric acids; reduction

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The chemo- and enantioselective reduction of alpha-imino esters with catecholborane has been developed employing 10 mol% of an enantiopure BINOL-based phosphoric acid as organocatalyst. Various differently substituted aromatic alpha-amino acid derivatives can be achieved in almost quantitative yields and very good to excellent enantioselectivities of up to 96% ee under mild reaction conditions.

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