Highly efficient asymmetric hetero-diels-alder reactions of carbonyl compounds catalyzed by Lewis acid platinum complexes of conformationally flexible NUPHOS-type diphosphines

Simon Doherty, Julian G. Knight, Christopher Hardacre, He Kuan Lou, Colin R. Newman, Rakesh K. Rath, Sarah Campbell, Mark Nieuwenhuyzen

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Conformationally flexible NUPHOS-type diphosphines have been resolved as their diastereopure platinum BINOLate complexes δ- and λ-[(NUPHOS)Pt{(S)-BINOL}] and the corresponding enantiopure Lewis acids δ- and λ-[(NUPHOS)Pt(OTf)2], being generated by protonation with trifluoromethanesulfonic acid, act as highly efficient catalysts for the hetero-Diels-Alder reaction of nonactivated conjugated dienes with aryl glyoxals and glyoxylate esters, giving ee's as high as 99%.

    Original languageEnglish
    Pages (from-to)6127-6133
    Number of pages7
    JournalOrganometallics
    Volume23
    Issue number26
    DOIs
    Publication statusPublished - 20 Dec 2004

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