Novel Asymmetric Wittig Reaction: Synthesis of Chiral Allenic Esters

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...

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Bibliographic Details
Published in:European journal of organic chemistry 2004-12, Vol.2004 (23), p.4830-4839
Main Authors: Pinho e Melo, Teresa M. V. D., Cardoso, Ana L., d'A. Rocha Gonsalves, António M., Costa Pessoa, João, Paixão, José A., Beja, Ana M.
Format: Article
Language:English
Subjects:
Asymmetric Wittig reaction
Chiral allenic esters
Chiral phosphorus ylides
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Summary: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)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200400413