Chiral Bis-π-allylpalladium Complex Catalyzed Asymmetric Allylation of Imines: Enhancement of the Enantioselectivity and Chemical Yield in the Presence of Water

Journal of the American Chemical Society

Volumn 125, Issue 46, 2003, Pages 14133-14139

  Fernandes, Rodney A ^a   Stimac, Anton ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLATION;

CATALYSIS; CATALYSTS; CRYSTALLIZATION; ISOMERIZATION; ISOMERS; SOLVENTS;

ALLYL RESINS;

PALLADIUM COMPLEX;

ALLYLATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CRYSTALLIZATION; ENANTIOSELECTIVITY; REPRODUCIBILITY; STEREOISOMERISM; STRUCTURE ANALYSIS;

EID: 0242497940     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja037272x     Document Type: Article

References (41)

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31. Olefin 7 (E:Z = 1:1) was prepared starting from (1S)-(-)-β-pinene available in Aldrich Chemical Co. in 97% ee. Though (IR)-(+)-nopinone (90% ee) is also available, we preferred to prepare it from (1S)-(-)-β-pinene by ozonolysis of exocyclic double bond. Further Wittig reaction with ethyltriphenylphosphonium bromide and BuOK gave 7 (E:Z = 1:1) [see: Brown, H. C.; Weissman, S. A.; Perumal, P. T.; Dhokte, U. P. J. Org. Chem. 1990, 55, 1217].
32. The solvents tried were 2-butanone, propionitrile, 2-propanol, and diisopropyl ether. Among all, propionitrile gave best upgradation ratio of 2a: 2b and recovery of catalyst during recrystalization. Though the catalyst is not freely soluble in propionitrile, warming to 90 °C gave clear solution. Higher temperatures or boiling should be avoided to prevent catalyst decomposition.
33. 1H NMR of 2a:2b = 1.3:1, 100:1, and >400:1.
34. 1H NMR spectrum available the ratio of the catalyst 2a:2b was 20:1. To the best of our knowledge, this is the first report of preparation of the catalyst 2a and separated from its undesired stereoisomer with a ratio of 2a:2b >400:1.
35. 3). See the Supporting Information for more details.
36. 3CN was added for better solubilization of stannane byproducts.
37. Details for each compound are giving in the Supporting Information.
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40. However, the enhancement of enantioselectivity by water is not clear. Formation of pentacoordinate Si is known, see reference (2), probably similar is the case with stannane.
41. A similar explanation is given by Hou, see: ref (2c).