Stereoselective Palladium-Catalyzed Carbocyclization of Allenic Allylic Carboxylates

Journal of the American Chemical Society

Volumn 125, Issue 46, 2003, Pages 14140-14148

  Franzén, Johan ^a   Löfstedt, Joakim ^a   Falk, Jennica ^a   Bäckvall, Jan E ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOCYCLIZATION; NUCLEOPHILIC ATTACK;

CARBOXYLIC ACIDS; CATALYSIS; CHEMICAL BONDS; ISOMERIZATION; PALLADIUM COMPOUNDS; SOLVENTS;

ALLYL RESINS;

CARBOXYLIC ACID DERIVATIVE; PALLADIUM;

ARTICLE; CARBOCYCLIZATION; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0242666400     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja037398u     Document Type: Article

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47. To succeed in the coupling reaction of bromoallene with the acetate and benzoate analogues 2, it was essential that the sodium hydride (60% dispersion in mineral oil) was of good quality. Sodium hydride that has been exposed to air moisture can contain substantial amounts of sodium hydroxide, which leads to degradation of the acetate and benzoate analogues 2 most likely via hydrolysis of the ester functions under the reaction condition used (see Scheme 2). However, the pivalic analogues of 2 were not sensitive to the quality of the sodium hydride due to steric hindrance toward hydrolysis from the tert-butyl-group.
48. The stereochemistry of the bridgehead protons has not been assigned.
49. 2 to yield trans-19.
50. This is in accordance with a more positive ΔS† for the oxidative addition pathway.
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65. This involves dissociation of palladium(0) from (π-olefin)palladium intermediate and trapping of the carbonium ion. Transient free Pd(0) complex may help in this trapping.
66. The pivalate released in the oxidative addition re-adds to the formed π-allyl in 30.
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68. Isomerization could occur either via a palladium(0)-catalyzed route (Granberg, K. L.; Bäckvall, J. E. J. Am. Chem. Soc. 1992, 114, 6858) or via a syn re-addition of the leaving-group (Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1980, 102, 4730).
69. 4 has electronic properties similar to those of bis-[(π-allyl)PdCl]. Åkermark, B.; Krakenberger, B.; Hansson, S. Organometallics 1987, 6, 620. It has also been shown that bis-[(π-allyl)PdCl] inserts into allenes. See ref 17f.
70. 3CN. reflux) had no effect on the outcome of the reaction, and cis-17 was observed as the only product.
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