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Title: Metal template effects on the asymmetric cycloaddition reaction between diphenylvinylphosphine and 2-diphenylphosphinofuran
Authors: Yeo, W.-C. 
Vittal, J.J. 
White, A.J.P.
Williams, D.J.
Leung, P.-H. 
Issue Date: 28-May-2001
Citation: Yeo, W.-C., Vittal, J.J., White, A.J.P., Williams, D.J., Leung, P.-H. (2001-05-28). Metal template effects on the asymmetric cycloaddition reaction between diphenylvinylphosphine and 2-diphenylphosphinofuran. Organometallics 20 (11) : 2167-2174. ScholarBank@NUS Repository.
Abstract: The organoplatinum complex containing ortho-metalated (S)-(1-(dimethylamino)ethyl)-naphthalene as the chiral auxiliary has been used efficiently to promote the asymmetric [4 + 2] Diels-Alder reaction between diphenylvinylphosphine and 2-diphenylphosphinofuran to generate the chelating diphosphine exo-cycloadduct, 4(R)-bis(diphenylphosphino)-7-oxabicyclo[2.2.1]hept-2-ene in 70% isolated yield. At room temperature, the reaction was complete in 5 d. However, the cycloaddition reaction proceeded at a significantly slower rate and exhibited a markedly lower stereoselectivity when the chiral platinum template was replaced by its organopallodium counterpart. The diphosphino-substituted oxanorbornene metal complexes are stable and the oxygen-carbon bonds are inert toward treatments with strong acids. Upon liberation from the metal ions, however, the chiral cycloadduct becomes unstable and undergoes the retro Diels-Alder reaction slowly to regenerate diphenylvinylphosphine and 2-diphenylphosphinofuran.
Source Title: Organometallics
ISSN: 02767333
DOI: 10.1021/om001063t
Appears in Collections:Staff Publications

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