Contribution to the synthesis of chiral allenic esters

• Author(s): Melo, Teresa M. V. D. Pinho e ; Cardoso, Ana L. ; Gonsalves, António M. D'A. Rocha ; Storr, Richard C. ; Pessoa, João Costa ; Paixão, José A. ; Beja, Ana M. ; Silva, Manuela Ramos
• Date: 2003
• Persistent ID: http://hdl.handle.net/10316/5157
• Origin: Estudo Geral - Universidade de Coimbra
• Subject(s): asymmetric Wittig reaction; chiral allenes; chiral phosphorus ylides
• Document Type: Article
• Language: English

Description

A phosphorus ylide bearing a 10-phenylsulfonylisoborneol unit reacted with ketenes, generated in situ from acid chlorides and triethylamine, to give allenic compounds. The reaction with methylketene led to asymmetric induction with the selective synthesis of an allene with axial chirality corresponding to an S configuration. The structure of the chiral allene 10-phenylsulfonylisobornyl penta-2,3-dienoate was determined by X-ray crystallography. Chirooptical studies of the chiral allene derivatives were done. http://www.sciencedirect.com/science/article/B6THS-495V85W-H/1/c946b9b7c8443e7586a0402c58d86df2