Platinum-catalyzed amidocarbonylation

Chemistry Letters

Volumn 32, Issue 2, 2003, Pages 160-161

  Sagae, Takahiro ^a   Sugiura, Masaharu ^a   Hagio, Hiroyuki ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMIDE; AMINO ACID DERIVATIVE; CARBON MONOXIDE; CARBONYL DERIVATIVE; LIGAND; PALLADIUM; PHOSPHINE DERIVATIVE; PLATINUM;

ACCELERATION; ARTICLE; CATALYSIS; EPIMERIZATION; RACEMIC MIXTURE;

EID: 0037545764     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2003.160     Document Type: Article

References (15)

1. For an excellent review, see: M. Beller and M. Eckert, Angew. Chem., Int. Ed., 39, 1010 (2000).
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5. It was described in a review (ref. 1) that a low enantioselectivity (10% ee) was attained by using 1-diphenylphosphanylethylbenzene as a chiral ligand in palladium-catalyzed amidocarbonylation.
6. 4).
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11. b) For a review, see: T. Hayashi, Acc. Chem. Res., 33, 354 (2000).
12. The intermediary of enamides in palladium-catalyzed amidocarbonylation was reported, see: D. A. Freed and M. C. Kozolwski, Tetrahedron Lett., 42, 3403 (2001).
13. 4 itself promoted the racemization under the reaction conditions. On the other hand, Beller et al. reported that rhodium or palladium complexes catalyzed the racemization of N-acyl α-amino acids, see: a) M. J. Hateley, D. A. Schichl, H. Kreusfeld, and M. Beller, Tetrahedron Lett., 41, 3821 (2000). b) M. J. Hateley, D. A. Schichl, C. Fischer, and M. Beller, Synlett, 2001, 25.
14. 4 itself promoted the racemization under the reaction conditions. On the other hand, Beller et al. reported that rhodium or palladium complexes catalyzed the racemization of N-acyl α-amino acids, see: a) M. J. Hateley, D. A. Schichl, H. Kreusfeld, and M. Beller, Tetrahedron Lett., 41, 3821 (2000). b) M. J. Hateley, D. A. Schichl, C. Fischer, and M. Beller, Synlett, 2001, 25.
15. 4, filtered, and concentrated in vacuo. The crystalline residue was washed with diethyl ether, collected by filtration, and dried under vacuum to give an analytically pure N-acyl amino acid.