1,4-Bis(arylsulfonyl)-1,2,3,4-tetrahydropyridines in Synthesis: Stereoselective Homo- and Hetero-Diels-Alder Reactions

Jean-Claude Adelbrecht; Donald Craig; Alice J. Fleming; Fionna M. Martin

doi:10.1055/s-2005-917073

LETTER

1,4-Bis(arylsulfonyl)-1,2,3,4-tetrahydropyridines in Synthesis: Stereoselective Homo- and Hetero-Diels-Alder Reactions

Jean-Claude Adelbrecht^a, Donald Craig*^a, Alice J. Fleming^a, Fionna M. Martin^b
^a Department of Chemistry, Imperial College London, South Kensington Campus, London SW7 2AZ, UK
Fax: +44(20)75945868; e-Mail: d.craig@imperial.ac.uk;
^b Eli Lilly & Co., Lilly Research Centre, Erl Wood Manor, Sunninghill Road, Windlesham, Surrey GU20 6PH, UK

Abstract

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Abstract

Palladium-catalysed coupling of a vinylstannane or vinyl boronic acids with 5-iodo-1,4-bis(tosyl)-1,2,3,4-tetrahydropyridines yields 1,3-dienes. These participate in homo- and hetero-Diels-Alder reactions with unsaturated carbonyl compounds and with nitroso species generated in situ to give novel bicyclic compounds in a highly stereoselective fashion.

Key words

Diels-Alder reaction - nitroso dienophile - palladium-catalysed coupling - stereoselective synthesis - tetrahydropyridine

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Referenzen

References

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8

We thank Dr. A. J. P. White (Imperial College) for the X-ray structure determinations. Full details will be reported elsewhere.

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12

Nitrosobenzene was purchased from Aldrich Chemical Co. and used as supplied.