organocatalyzed asymmetric α-oxidation, α-aminoxylation and α-amination of carbonyl compoundsorganocatalyzed非对称α-oxidation,α-aminoxylation和α-amination羰基化合物.pdf

Molecules 2010, 15, 917-958; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Review Organocatalyzed Asymmetric -Oxidation, -Aminoxylation and -Amination of Carbonyl Compounds Tirayut Vilaivan * and Worawan Bhanthumnavin Organic Synthesis Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Phayathai Road, Patumwan, Bangkok 10330, Thailand; E-Mail: worawan.b@chula.ac.th (W.B.) * Author to whom correspondence should be addressed; E-Mail: vtirayut@chula.ac.th. Received: 25 December 2009; in revised form: 27 January 2010 / Accepted: 5 February 2010 / Published: 11 Februray 2010 Abstract: Organocatalytic asymmetric -oxidation and amination reactions of carbonyl compounds are highly useful synthetic methodologies, especially in generating chiral building blocks that previously have not been easily accessible by traditional methods. The concept is relatively new and therefore the list of new catalysts, oxidizing and aminating reagents, as well as new substrates, are expanding at an amazing rate. The scope of this review includes new reactions and catalysts, mechanistic aspects and synthetic applications of -oxidation, hydroxylation, aminoxylation, amination, hydrazination, hydroxyamination and related -heteroatom functionalization of aldehydes, ketones and related active methylene compounds published during 2005–2009. Keywords: organocatalyst; chiral catalyst; -oxidation; -amination; -aminoxylation; nitrosoaldol rea