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Title: Novel Asymmetric Wittig Reaction: Synthesis of Chiral Allenic Esters
Authors: Melo, Teresa M. V. D. Pinho e 
Cardoso, Ana L. 
Gonsalves, António M. d'A. Rocha 
Pessoa, João Costa 
Paixão, José A. 
Beja, Ana M. 
Issue Date: 2004
Citation: European Journal of Organic Chemistry. 2004:23 (2004) 4830-4839
Abstract: Wittig reactions between 10-(phenylsulfonyl)isobornyl (triphenylphosphoranylidene)acetates (1 and 6) and ketenes resulted in asymmetric induction, with the selective synthesis of allenes with axial chirality. Use of the (1R)-(-)-10-(phenylsulfonyl)isoborneol unit allows the synthesis of allenes with S configuration, whereas use of the (1S)-(+)-10-(phenylsulfonyl)isoborneol unit produces allenes with R configuration. The structure of (1R)-(-)-10-(phenylsulfonyl)isobornyl (S)-5,5-dimethylhexa-2,3-dienoate (2e) was determined by X-ray crystallography. Chirooptical studies of the allenic esters were carried out, confirming that two sets of enantiomeric derivatives were obtained. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
DOI: 10.1002/ejoc.200400413
Rights: openAccess
Appears in Collections:FCTUC Química - Artigos em Revistas Internacionais

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