Complementary reactions of allylic carbamates using palladium(II): Formation of oxazolidinones or allylic amides from a common precursor

Synthesis

Volumn , Issue 1, 2009, Pages 148-154

  Christie, Steven D R ^a   Warrington, Adam D ^a   Lunniss, Christopher J ^b  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Amides; Amines; Halogenation; Palladium; Rearrangement

Indexed keywords

OXAZOLIDINONES; REARRANGEMENT; SIGMATROPIC REARRANGEMENTS; STARTING MATERIALS; TO EFFECTS;

AMIDES; AMINATION; AMINES; HALOGENATION; PALLADIUM COMPOUNDS;

PALLADIUM;

(2,2,2 TRICHLOROACETYL)CARBAMIC ACID; 2,2,2 TRICHLORO N (3 PHENYLALLYL)ACETAMIDE; 2,2,2 TRICHLORO N (4 METHYLPENT 2 ENYL)ACETAMIDE; 2,2,2 TRICHLORO N (4 PHENYLBUT 2 ENYL)ACETAMIDE; 2,2,2 TRICHLORO N (5 PHENYLPENT 2 ENYL)ACETAMIDE; 2,2,2 TRICHLORO N [3 (4 NITROPHENYL)ALLYL]ACETAMIDE; 2,2,2 TRICHLORO N CYCLOHEX 2 ENYLACETAMIDE; 2,2,2 TRICHLORO N PENT 2 ENYLACETAMIDE; 2,2,2 TRICHLORO N PENTA 2,4 DIENYLACETAMIDE; 4 CHLOROMETHYL 5 ETHYLOXAZOLIDIN 2 ONE; 4 CHLOROMETHYL 5 ISOPROPYLOXAZOLIDIN 2 ONE; 4 CHLOROMETHYL 5 PHENETHYLOXAZOLIDIN 2 ONE; 4 CHLOROMETHYL 5 PHENYLOXAZOLIDIN 2 ONE; 4 CHLOROMETHYL 5 VINYLOXAZOLIDIN 2 ONE; 5 ALLYL 4 CHLOROMETHYLOXAZOLIDIN 2 ONE; ALKENE; ALLYL COMPOUND; AMIDE; CARBAMIC ACID; CARBAMIC ACID 3 PHENYLALLYL ESTER; COPPER; N ALLYL 2,2,2 TRICHLOROACETAMIDE; OSMIUM; OXAZOLIDINONE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHLORINATION; CONTROLLED STUDY; CYCLIZATION; DEPROTECTION REACTION; HALOGENATION; HYDROXYLATION; MICROWAVE RADIATION; SUBSTITUTION REACTION;

EID: 63849191340     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0028-1083282     Document Type: Article

References (15)

1. Christie, S. D. R.; Warrington, A. D. Synthesis 2008, 1325.
2. Liu, G.; Stahl, S. S. J. Am. Chem. Soc. 2006, 128, 7179.
3. Alexanian, E. J.; Lee, C.; Sorensen, E. J. J. Am. Chem. Soc. 2005, 127, 7690.
4. Donohoe, T. J.; Johnson, P. D.; Helliwell, M.; Keenan, M. Chem. Commun. 2001, 2078.
5. Lei, A.; Lu, X.; Liu, G. Tetrahedron Lett. 2004, 45, 1785.
6. Manzoni, M. R.; Zabawa, T. P.; Kasi, D.; Chemler, S. R. Organometallics 2004, 23, 5618.
7. Michael, F. E.; Sibbald, P. A.; Cochran, B. M. Org. Lett. 2008, 10, 793.
8. Lei, A.; Lu, X. Org. Lett. 2000, 2, 2357.
9. (a) Overman, L. E. Acc. Chem. Res. 1980, 13, 218.
10. (b) Nubbemeyer, N. Synthesis 2003, 961.
11. For a related example, see: Garner, P.; Park, J. M. J. Org. Chem. 1988, 53, 2979.
12. Bach, T.; Eckhardt, M.; Furlong, M.; Knoess, H. P.; Berger, S.; Knochel, P. Tetrahedron 1994, 50, 2415.
13. Ali, I. A. I.; El Ashry, E. S. H.; Schmidt, R. R. Tetrahedron 2004, 60, 4773.
14. Overman, L. E. J. Am. Chem. Soc. 1976, 98, 2901.
15. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley and Sons: New York, 1999.