1,4-Bis(arylsulfonyl)-1,2,3,4-tetrahydropyridines in synthesis: Stereoselective homo- and hetero-Diels-Alder reactions

Synlett

Volumn , Issue 17, 2005, Pages 2643-2647

  Adelbrecht, Jean Claude ^a   Craig, Donald ^a   Fleming, Alice J ^a   Martin, Fionna M ^b  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

Diels Alder reaction; Nitroso dienophile; Palladium catalysed coupling; Stereoselective synthesis; Tetrahydropyridine

Indexed keywords

1 TOLYLSULFONYL 2 (1 METHYLETHYL)AZIRIDINE; 1 TOLYLSULFONYL 3,3 DIMETHOXYPROPANE; 1,4 BIS(SULFONYL) 1,2,3,4 TETRAHYDROPYRIDINE; 2 (1 METHYLETHYL) 1,4 BIS (4 TOLYLSULFONYL) 1,2,3,4,5,6,7,8A OCTAHYDROQUINOLINE 8 CARBALDEHYDE; 2 (1 METHYLETHYL) 1,4 BIS(4 TOLYLSULFONYL) 5 VINYL 1,2,3,4 TETRAHYDROPYRIDINE; 2 ISOPROPYL 1,4 BIS (TOLUENE 4 SULFONYL) 5 VINYL 1,2,3,4 TETRAHYDROPYRIDINE; 3,5 DINITROBENZOATE ESTER; 5 ALKENYL 1,4 BIS(4 TOLYLSULFONYL) 1,2,3,4 TETRAHYDROPYRIDINES; AZIRIDINE DERIVATIVE; BORONIC ACID DERIVATIVE; CARBONYL DERIVATIVE; E 2 PHENYLETHENYLBORONIC ACID; ESTER DERIVATIVE; N CARBAMOYL 2,3 DIHYDRO 4 PYRIDONES; PALLADIUM; PROPANE; PYRIDINE DERIVATIVE; PYRIDONE DERIVATIVE; TIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; DIELS ALDER REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 27444433418     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-917073     Document Type: Article

References (20)

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8. For anionic addition reactions to N-heterocyclic 1,3-dienes derived from aminoacids, see: Carballares, S.; Craig, D. J. Organomet. Chem. 2001, 624, 381.
9. 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: (a) Kuethe, J. T.; Brooks, C. A.; Comins, D. L. Org. Lett. 2003, 5, 321.
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15. We thank Dr. A. J. P. White (Imperial College) for the X-ray structure determinations. Full details will be reported elsewhere.
16. Williams, M. R. V. PhD Thesis; University of London: UK, 1998.
17. For reviews of the nitroso-Diels-Alder reaction and leading references, see: (a) Yamamoto, H.; Momiyama, N. Chem. Commun. 2005, 3514.
18. (b) Vogt, P. F.; Miller, M. J. Tetrahedron 1998, 54, 1317.
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20. Nitrosobenzene was purchased from Aldrich Chemical Co. and used as supplied.