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

doi:10.1021/om049392z

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	6127-6133
Number of pages	7
Journal	Organometallics
Volume	23
Issue number	26
DOIs	https://doi.org/10.1021/om049392z
Publication status	Published - 20 Dec 2004

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10.1021/om049392z

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Doherty, S., Knight, J. G., Hardacre, C., Lou, H. K., Newman, C. R., Rath, R. K., Campbell, S., & Nieuwenhuyzen, M. (2004). Highly efficient asymmetric hetero-diels-alder reactions of carbonyl compounds catalyzed by Lewis acid platinum complexes of conformationally flexible NUPHOS-type diphosphines. Organometallics, 23(26), 6127-6133. https://doi.org/10.1021/om049392z

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

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%.",

author = "Simon Doherty and Knight, {Julian G.} and Christopher Hardacre and Lou, {He Kuan} and Newman, {Colin R.} and Rath, {Rakesh K.} and Sarah Campbell and Mark Nieuwenhuyzen",

year = "2004",

month = dec,

day = "20",

doi = "10.1021/om049392z",

language = "English",

volume = "23",

pages = "6127--6133",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "26",

}

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, Julian G.; Hardacre, Christopher et al.
In: Organometallics, Vol. 23, No. 26, 20.12.2004, p. 6127-6133.

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

TY - JOUR

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, Julian G.

AU - Hardacre, Christopher

AU - Lou, He Kuan

AU - Newman, Colin R.

AU - Rath, Rakesh K.

AU - Campbell, Sarah

AU - Nieuwenhuyzen, Mark

PY - 2004/12/20

Y1 - 2004/12/20

N2 - 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%.

AB - 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%.

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DO - 10.1021/om049392z

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AN - SCOPUS:11044226706

SN - 0276-7333

VL - 23

SP - 6127

EP - 6133

JO - Organometallics

JF - Organometallics

IS - 26

ER -

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

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CCDC 260128: Experimental Crystal Structure Determination

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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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CCDC 260128: Experimental Crystal Structure Determination

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