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

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Synlett 2005(17): 2643-2647
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

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Publication History

Received 21 July 2005
Publication Date:
05 October 2005 (online)

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

References

1a Craig D. McCague R. Potter GA. Williams MRV. Synlett 1998, 55

Article in Thieme Connect Google Scholar
1b Craig D. McCague R. Potter GA. Williams MRV. Synlett 1998, 58

Article in Thieme Connect Google Scholar
1c Adelbrecht J.-C. Craig D. Thorimbert S. Tetrahedron Lett. 2001, 42: 8369

Article in Thieme Connect Google Scholar
1d Adelbrecht J.-C. Craig D. Dymock BW. Thorimbert S. Synlett 2000, 467

Article in Thieme Connect Google Scholar
2 Berry MB. Craig D. Synlett 1992, 41

Article in Thieme Connect Google Scholar
3a Brosius AD. Overman LE. Schwink L. J. Am. Chem. Soc. 1999, 121: 700

Crossref Google Scholar
3b For a related approach, see: Passarella D. Angoli M. Giardini A. Lesma G. Silvani A. Danieli B. Org. Lett. 2002, 4: 2925

Crossref Google Scholar
4 For anionic addition reactions to N-heterocyclic 1,3-dienes derived from aminoacids, see: Carballares S. Craig D. J. Organomet. Chem. 2001, 624: 381

Google Scholar
During the early stages of this work Comins and co-workers reported highly stereoselective [4+2] cycloaddition reactions of N-carbamoyl-2,3-dihydro-4-pyridones possessing alkenyl groups at the 5-position. See:
5a Kuethe JT. Brooks CA. Comins DL. Org. Lett. 2003, 5: 321

Crossref PubMed Google Scholar
5b Kuethe JT. Comins DL. Tetrahedron Lett. 2003, 44: 4179

Crossref PubMed Google Scholar
5c Comins DL. Kuethe JT. Miller TM. Fevrier FC. Brooks CA. J. Org. Chem. 2005, 70: 5221

Crossref PubMed Google Scholar
6 Comins DL. Joseph SP. Chen X. Tetrahedron Lett. 1995, 36: 9141

Crossref Google Scholar
7a Angara GJ. McNelis E. Tetrahedron Lett. 1991, 32: 2099

Crossref Google Scholar
7b Bovonsombat P. Angara GJ. McNelis E. Tetrahedron Lett. 1994, 35: 6787

Crossref Google Scholar
9 Williams MRV. PhD Thesis University of London; UK: 1998.

Google Scholar
For reviews of the nitroso-Diels-Alder reaction and leading references, see:
10a Yamamoto H. Momiyama N. Chem. Commun. 2005, 3514

Crossref Google Scholar
10b Vogt PF. Miller MJ. Tetrahedron 1998, 54: 1317

Crossref Google Scholar
11 Santianello E. Manzocchi A. Farachi C. Synthesis 1980, 563

Article in Thieme Connect Google Scholar

8

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

12

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