Synthesis of homoallylic alcohols via palladium-catalyzed three-component coupling of an arylboronic acid with allenes and aldehydes

Organic Letters

Volumn 6, Issue 13, 2004, Pages 2221-2224

  Hopkins, Chad D ^a   Malinakova, Helena C ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALDEHYDE DERIVATIVE; ALLENE DERIVATIVE; BORONIC ACID DERIVATIVE; PALLADIUM;

ALCOHOL OXIDATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CROSS COUPLING REACTION; MOLECULAR INTERACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 3142735839     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0492795     Document Type: Article

References (51)

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14. For a nickel-catalyzed coupling of allenyl aldehydes and alkylzincs, see: (a) Montgomery, J.; Song, M. Org. Lett. 2002, 4, 4009-4011. Attempted intermolecular three-component coupling with an arylzinc afforded benzylic alcohols via a direct addition of arylzincs to aldehydes, see: (b) Montgomery, J.; Oblinger, E. J. Am. Chem. Soc. 1997, 119, 9065-9066. An example of a nickel-catalyzed coupling of boronic acids with alkynes and imines yielding allylic amines is known; see: (c) Patel, S. J.; Jamison, T, F. Angew. Chem., Int. Ed. 2003, 42, 1364-1367. For additional related nickel-catalyzed multicomponent coupling reactions, see: (d) Molinary, C.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 8076-8077. (e) Montgomery, J. Acc. Chem. Res. 2000, 33, 467-473. (f) Mori, M.; Takimoto, M.; Sato, Y. J. Am. Chem. Soc. 2000, 122, 1624-1634. (g) Ikeda, S.-I. Angew. Chem., Int. Ed. 2003, 42, 5120-5122.
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17. For a nickel-catalyzed coupling of allenyl aldehydes and alkylzincs, see: (a) Montgomery, J.; Song, M. Org. Lett. 2002, 4, 4009-4011. Attempted intermolecular three-component coupling with an arylzinc afforded benzylic alcohols via a direct addition of arylzincs to aldehydes, see: (b) Montgomery, J.; Oblinger, E. J. Am. Chem. Soc. 1997, 119, 9065-9066. An example of a nickel-catalyzed coupling of boronic acids with alkynes and imines yielding allylic amines is known; see: (c) Patel, S. J.; Jamison, T, F. Angew. Chem., Int. Ed. 2003, 42, 1364-1367. For additional related nickel-catalyzed multicomponent coupling reactions, see: (d) Molinary, C.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 8076-8077. (e) Montgomery, J. Acc. Chem. Res. 2000, 33, 467-473. (f) Mori, M.; Takimoto, M.; Sato, Y. J. Am. Chem. Soc. 2000, 122, 1624-1634. (g) Ikeda, S.-I. Angew. Chem., Int. Ed. 2003, 42, 5120-5122.
18. For a nickel-catalyzed coupling of allenyl aldehydes and alkylzincs, see: (a) Montgomery, J.; Song, M. Org. Lett. 2002, 4, 4009-4011. Attempted intermolecular three-component coupling with an arylzinc afforded benzylic alcohols via a direct addition of arylzincs to aldehydes, see: (b) Montgomery, J.; Oblinger, E. J. Am. Chem. Soc. 1997, 119, 9065-9066. An example of a nickel-catalyzed coupling of boronic acids with alkynes and imines yielding allylic amines is known; see: (c) Patel, S. J.; Jamison, T, F. Angew. Chem., Int. Ed. 2003, 42, 1364-1367. For additional related nickel-catalyzed multicomponent coupling reactions, see: (d) Molinary, C.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 8076-8077. (e) Montgomery, J. Acc. Chem. Res. 2000, 33, 467-473. (f) Mori, M.; Takimoto, M.; Sato, Y. J. Am. Chem. Soc. 2000, 122, 1624-1634. (g) Ikeda, S.-I. Angew. Chem., Int. Ed. 2003, 42, 5120-5122.
19. For a nickel-catalyzed coupling of allenyl aldehydes and alkylzincs, see: (a) Montgomery, J.; Song, M. Org. Lett. 2002, 4, 4009-4011. Attempted intermolecular three-component coupling with an arylzinc afforded benzylic alcohols via a direct addition of arylzincs to aldehydes, see: (b) Montgomery, J.; Oblinger, E. J. Am. Chem. Soc. 1997, 119, 9065-9066. An example of a nickel-catalyzed coupling of boronic acids with alkynes and imines yielding allylic amines is known; see: (c) Patel, S. J.; Jamison, T, F. Angew. Chem., Int. Ed. 2003, 42, 1364-1367. For additional related nickel-catalyzed multicomponent coupling reactions, see: (d) Molinary, C.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 8076-8077. (e) Montgomery, J. Acc. Chem. Res. 2000, 33, 467-473. (f) Mori, M.; Takimoto, M.; Sato, Y. J. Am. Chem. Soc. 2000, 122, 1624-1634. (g) Ikeda, S.-I. Angew. Chem., Int. Ed. 2003, 42, 5120-5122.
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31. Following an "unproductive" transfer of the 2-propenyl group in the first turnover, catalyst 1a was expected to yield the symmetrical bisπ-allylpalladium complex VII (Figure 1).
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35. H1-H2 = 8-50 Hz in the minor diastereomer 5b) were consistent with dihedral angles anticipated in the most stable conformations of syn and anti diastereomers of alcohol 5, respectively.
36. H1-H2 = 4.88 Hz was reported; see: ref 8f.
37. For the effect of substitution on the relative transfer abilities of allyl ligands in bis-π-allylpalladium complexes, see: (a) Reference 3. (b) Solin, N.; Narayan, S.; Szabó, K. J. J. Org. Chem. 2001, 66, 1686-1693.
38. For the effect of substitution on the relative transfer abilities of allyl ligands in bis-π-allylpalladium complexes, see: (a) Reference 3. (b) Solin, N.; Narayan, S.; Szabó, K. J. J. Org. Chem. 2001, 66, 1686-1693.
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40. (l 8) For asymmetric allylation of imines catalyzed by analogues of complex 1b, see: (a) Fernandes, R. A.; Stimac, A.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 14133-14139. (b) Nakamura, H.; Nakamura, K.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 4242-4243.
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42. 3 (Pd:P, 1:1) limited the yields of alcohols 5 to 6% and 9%, respectively, although precipitation of Pd(0) was eliminated.
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44. In asymmetric allylations of imines, catalyst 1b proved to be less effective than its more substituted derivatives; see: ref 18b.
45. 1H NMR spectra of alcohol 10, the syn/anti assignments for 10 remain tentative.
46. Determined by chiral-phase HPLC.
47. (a) In allylations catalyzed by bis-π-allylpalladium complexes, prior coordination of electrophiles to palladium was proposed to occur under "phosphine free" conditions; see references 3 and 8b. Lower diastereoselectivity for the anti product was noted in analogous allylations in the presence of phosphine; see: Wallner, O. A.; Szabó, K. J. Org. Lett. 2002, 4, 1563-1566.
48. (c) For allylations via "open" transition states yielding syn products, see: Hayashi, T.; Kabeta, K.; Hamachi, I.; Kumada, M. Tetrahedron Lett. 1983, 24, 2865-2868.
49. 3B) is known; see reference 8d.
50. (a) Soling, N.; Kjellgren, J.; Szabó, K. J. Angew. Chem., Int. Ed. 2003, 42, 3656-3658.
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