Asymmetric Carroll rearrangement of allyl α-acetamido-β- ketocarboxylates catalysed by a chiral palladium complex

Chemical Communications

Volumn , Issue 31, 2005, Pages 3951-3952

  Kuwano, Ryoichi ^a,b   Ishida, Naoki ^a   Murakami, Masahiro ^a  

^a KYOTO UNIVERSITY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA ACETAMIDO BETA KETOCARBOXYLATE DERIVATIVE; AMINOKETONE; CARBOXYLIC ACID; PALLADIUM COMPLEX; PHOSPHINE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CARROLL REARRANGEMENT; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; DECARBOXYLATION; ENANTIOSELECTIVITY; OPTICS; REACTION ANALYSIS;

EID: 23944465698     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b505105c     Document Type: Article

References (18)

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11. For asymmetric Carroll rearrangement by using stoichiometric SAMP or RAMP, see: D. Enders and M. Knopp, Tetrahedron, 1996, 52, 5805.
12. Very recently, two groups reported enantioselective decarboxylative intramolecular allylation of cycloalkanones: (a) D. C. Behenna and B. M. Stoltz, J. Am. Chem. Soc., 2004, 126, 15044;
13. (b) B. M. Trost and J. Xu, J. Am. Chem. Soc., 2005, 127, 2846.
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16. B. M. Trost and R. C. Bunt, Angew. Chem., Int. Ed. Engl., 1996, 35, 99.
17. The chiral ligand 3 is commercially available from Strem Chemicals, Inc. 9 It might be that hydrogen bonding between the protic hydrogens with the amido groups of 3 favors a desired conformation or disfavors undesired amido coordination to palladium. For a similar effect of alcohol addition to improve an enantioselectivity, see: B. M. Trost, C. P. Soldermann, I. Chen and G. M. Schroeder, J. Am. Chem. Soc., 2004, 126, 4480.
18. We assumed that the acetamido group serves to fix the transition state conformation, probably through interaction with the cationic palladium center.