Organocatalytic Michael Reaction of Nitroenamine Derivatives with Aldehydes: Short and Efficient Asymmetric Synthesis of (−)-Oseltamivir

• Published in: ChemCatChem Vol. 4; no. 7; pp. 1007 - 1012
• Main Authors: Weng, Jiang, Li, Yong-Bo, Wang, Rui-Bin, Lu, Gui
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.07.2012; WILEY‐VCH Verlag; Wiley Subscription Services, Inc
• Subjects: asymmetric synthesis; Michael addition; nitroenamines; organocatalysis; oseltamivir
• ISSN: 1867-3880; 1867-3899
• DOI: 10.1002/cctc.201200124

Nitroenamine derivatives were used as a new class of Michael acceptors in the organocatalytic Michael reaction of aldehydes. The addition products were obtained in good yields and very good to excellent enantioselectivities. Moreover, a highly efficient, enantioselective, and simple synthesis of (−)‐oseltamivir was accomplished in only five steps: two separate one‐pot operations and one purification step. This procedural simplicity demonstrated the power of the organocatalytic asymmetric Michael reaction of nitroenamine acceptors with aldehydes. Give it a nitro boost! Nitroenamine derivatives were used as a new class of Michael acceptors in the organocatalytic Michael reaction. Moreover, a highly efficient and simple synthesis of (−)‐oseltamivir was accomplished in only a five‐step synthesis.