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

Simon Doherty; J.G. Knight; Christopher Hardacre; H.K. Lou; C.R. Newman; Rakesh Rath; S. Campbell; Mark Nieuwenhuyzen

doi:10.1021/om04392z

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

Simon Doherty, J.G. Knight, Christopher Hardacre, H.K. Lou, C.R. Newman, Rakesh Rath, S. Campbell, Mark Nieuwenhuyzen

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article › peer-review

26 Citations (Scopus)

Abstract

Conformationally flexible NUPHOS-type diphosphines have been resolved as their diastereopure platinum BINOLate complexes delta- and lambda-[(NUPHOS)Pt{(S)-BINOL}] and the corresponding enantiopure Lewis acids delta- and lambda-[(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 language	English
Pages (from-to)	6127-6133
Number of pages	7
Journal	Organometallics
Volume	23
Issue number	26
DOIs	https://doi.org/10.1021/om04392z
Publication status	Published - 20 Dec 2004

ASJC Scopus subject areas

Inorganic Chemistry
Organic Chemistry

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Doherty, Simon ; Knight, J.G. ; Hardacre, Christopher ; Lou, H.K. ; Newman, C.R. ; Rath, Rakesh ; Campbell, S. ; Nieuwenhuyzen, Mark. / Highly efficient asymmetric hetero-Diels-Alder reactions of carbonyl compounds catalyzed by Lewis acid platinum complexes of conformationally flexible NUPHOS-type diphosphines. In: Organometallics. 2004 ; Vol. 23, No. 26. pp. 6127-6133.

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abstract = "Conformationally flexible NUPHOS-type diphosphines have been resolved as their diastereopure platinum BINOLate complexes delta- and lambda-[(NUPHOS)Pt{(S)-BINOL}] and the corresponding enantiopure Lewis acids delta- and lambda-[(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%.",

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Highly efficient asymmetric hetero-Diels-Alder reactions of carbonyl compounds catalyzed by Lewis acid platinum complexes of conformationally flexible NUPHOS-type diphosphines. / Doherty, Simon; Knight, J.G.; Hardacre, Christopher; Lou, H.K.; Newman, C.R.; Rath, Rakesh; Campbell, S.; Nieuwenhuyzen, Mark.

In: Organometallics, Vol. 23, No. 26, 20.12.2004, p. 6127-6133.

Research output: Contribution to journal › Article › peer-review

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T1 - Highly efficient asymmetric hetero-Diels-Alder reactions of carbonyl compounds catalyzed by Lewis acid platinum complexes of conformationally flexible NUPHOS-type diphosphines

AU - Doherty, Simon

AU - Knight, J.G.

AU - Hardacre, Christopher

AU - Lou, H.K.

AU - Newman, C.R.

AU - Rath, Rakesh

AU - Campbell, S.

AU - Nieuwenhuyzen, Mark

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AB - Conformationally flexible NUPHOS-type diphosphines have been resolved as their diastereopure platinum BINOLate complexes delta- and lambda-[(NUPHOS)Pt{(S)-BINOL}] and the corresponding enantiopure Lewis acids delta- and lambda-[(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%.

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

Abstract

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