title: Proline-tetrazole-catalyzed enantioselective N-nitroso aldol reaction of aldehydes with in situ generated nitrosocarbonyl compounds.
abstract: A highly enantioselective method (up to 98% ee) for the preparation of β-amino alcohols was achieved by using the readily available proline-tetrazole as the catalyst for the N-nitroso aldol reaction of aldehydes with in situ generated nitrosocarbonyl compounds. The key to success of this reaction is the use of MnO2 as an oxidant and catechol as a Brønsted acid additive.
authors.affiliation: Molecular Catalyst Research Center, Chubu University, 1200 Matsumoto-cho, Kasugai, Aichi 487-8501 (Japan) http://www3.chubu.ac.jp/catalyst/. biplabmaji@isc.chubu.ac.jp.
authors.forename: Biplab
authors.initials: B
authors.lastname: Maji
authors.forename: Hisashi
authors.initials: H
authors.lastname: Yamamoto
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000605:Amino Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D002396:Catechols / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D017895:Manganese Compounds / Q000737:chemistry; D009603:Nitroso Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D010087:Oxides / Q000737:chemistry; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism; D013777:Tetrazoles / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000605:Amino Alcohols; D002396:Catechols; D007659:Ketones; D017895:Manganese Compounds; D009603:Nitroso Compounds; D010087:Oxides; D013777:Tetrazoles; C027424:manganese oxide; C116609:3-hydroxybutanal; D011392:Proline; C034221:catechol
keywords: aldol reaction; amino alcohol; organocatalysis; oxidation; synthetic methods