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

28 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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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 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\%.",

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

year = "2004",

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doi = "10.1021/om04392z",

language = "English",

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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

PY - 2004/12/20

Y1 - 2004/12/20

N2 - 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%.

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%.

UR - https://www.scopus.com/pages/publications/11044226706

U2 - 10.1021/om04392z

DO - 10.1021/om04392z

M3 - Article

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

Abstract

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