Published in
Elsevier, Tetrahedron Letters, 34(44), p. 6409-6412
DOI: 10.1016/s0040-4039(03)01585-5
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Contribution to the Synthesis of Chiral Allenic Esters
,
Ana L. Cardoso,
António M. D ' A Rocha Gonsalves,
Richard C. Storr,
João Costa Pessoa,
José A. Paixão ,
Ana M. Beja,
Manuela Ramos Silva
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Abstract
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.