835869-62-0Relevant academic research and scientific papers
Novel asymmetric Wittig reaction: Synthesis of chiral allenic esters
Pinho E Melo, Teresa M. V. D.,Cardoso, Ana L.,Rocha Gonsalves, Antonio M. D'A.,Costa Pessoa, Joao,Paixao, Jose A.,Beja, Ana M.
, p. 4830 - 4839 (2007/10/03)
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-(phenyl-sulfonyl)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.
