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Volumn 122, Issue 33, 2000, Pages 7905-7920

Application of chiral mixed phosphorus/sulfur ligands to palladium-catalyzed allylic substitutions

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALLYL COMPOUND; BENZYLAMINE; LIGAND; MALONIC ACID DERIVATIVE; PALLADIUM; PHOSPHORUS; PIPERIDINE DERIVATIVE; PYRAN DERIVATIVE; SULFUR;

EID: 0034706036     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992543i     Document Type: Article
Times cited : (330)

References (99)
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    • P-chiral diphosphines also have stereogenicity close to the metal center. For examples of the application of the P-chiral diphosphine DIPAMP in asymmetric catalysis see: (a) Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D.; Weinkauff, D. J. J. Am. Chem. Soc. 1975, 97, 2567-2568. (b) Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L.; Weinkauff, D. J. J. Am. Chem. Soc. 1977, 99, 5946-5952.
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    • note
    • 2 bond between Pd and C2-C3.
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    • note
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    • While Pd-sparteine complexes catalyze the allylic alkylation of 1,3-diphenylpropenyl acetate in 75% ee, the corresponding alkylation on cyclohexenyl acetate proceeds in only 50% ee. (a) Togni, A. Tetrahedron: Asymmetry 1991, 2, 683-690. Similarly, chiral phenanthroline complexes were found to catalyze the allylic alkylation of 1,3-diphenylpropenyl acetate in 92% ee, but the alkylation of cyclohexenyl acetate proceeds in only 16% ee. (b) Pena-Cabrera, E.; Norrby, P.; Sjögren, M.; Vitagliano, A.; de Felice, V.; Oslob, J.; Ishii, S.; O'Neill, D.; Akermark, B.; Helquist, P. J. Am. Chem. Soc. 1996, 118, 4299-4313.
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    • The ligands developed by Trost are effective for the allylic alkylation of both cyclic and acyclic substrates; however, only acyclic substrates containing sterically small substituents gave high enantiomeric excesses. (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089-4090. (b) Knuehl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845-1846 and references therein. Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1998, 37, 3047-3050.
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    • 2 as the nucleophile in THF afforded good yields of 55a in 58% and 89% ee, respectively.
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    • When ligands 10k and 11k were used in the allylic alkylation of 1,4-diacetoxycyclopentene, the monoalkylated adduct was obtained in 91% and 62% ee, respectively.
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    • The most notable exception is the asymmetric palladium-catalyzed allylic substitution of cis-2,5-diacyloxy-2,5-dihydrofuran toward the synthesis of nucleosides. Trost, B. M.; Shi, Z. J. Am. Chem. Soc. 1996, 118, 3037-3038,
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    • 2,6-Diisopropylphenylimidoneophylidenemolybdenum(VI) bis(hexafluoro-tert-butoxide). Schrock, R. R. Pure Appl. Chem. 1994, 66, 1447-1454 and references therein.
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    • note
    • 3; Z = 4; R = 0.0433, GoF = 1.282.
  • 90
    • 0343418783 scopus 로고    scopus 로고
    • note
    • C1-C2 is shorter (1.36 Å) than C2-C3 (1.44 Å).
  • 91
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    • note
    • Geometry optimizations were performed at the PM3(tm) level using the Spartan Semiempirical Program 5.0 (Wavefunction Inc., Irvine, CA 92715) on a Silicon Graphics Impact 10000 (195 MHz, 128 M RAM) running IRIX 6.2. Calculations ere performed without counterions or solvent using these parameters: optcycle = 2000, maxcycle = 2000, charge = 0, multiplicity = 0. Calculations converged (energy difference between cycles <0.0005 kcal/mol) in ≤4 h CPU time.
  • 92
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    • note
    • 2 is small (<1.0 kcal/mol), making it difficult to (fetermine the nature of the drastic difference in the observed enantioselectivities in the allylic substitution of both acyclic and cyclic substrates.
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    • The most notable example of a minor diastereomeric complex reacting faster than the major was reported by Halpem in the rhodium-catalyzed hydrogenation of (Z)-acetamidocinnamates. (a) Halpern, J. Science 1982, 217, 401 -407. (b) Halpern, J.; Landis, C. R. J. Am. Chem. Soc. 1987, 109, 1746-1754 and references therein.
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    • The most notable example of a minor diastereomeric complex reacting faster than the major was reported by Halpem in the rhodium- catalyzed hydrogenation of (Z)-acetamidocinnamates. (a) Halpern, J. Science 1982, 217, 401 -407. (b) Halpern, J.; Landis, C. R. J. Am. Chem. Soc. 1987, 109, 1746-1754 and references therein.
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    • Halpern, J.1    Landis, C.R.2


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