Palladium-catalyzed enantioselective diboration of prochiral allenes

Journal of the American Chemical Society

Volumn 126, Issue 50, 2004, Pages 16328-16329

  Pelz, Nicholas F ^a   Woodward, Angela R ^a   Burks, Heather E ^a   Sieber, Joshua D ^a   Morken, James P ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; REACTION ANALYSIS;

ALKADIENES; BORON COMPOUNDS; CATALYSIS; ORGANOPHOSPHORUS COMPOUNDS; PALLADIUM; STEREOISOMERISM;

EID: 11444261871     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja044167u     Document Type: Article

References (33)

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12. (a) Ishiyama, T.; Kitano, T.; Miyaura, N. Tetrahedron Lett. 1998, 39, 2357.
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21. For a Pd(0)-catalyzed diboration that appears not to proceed by oxidative addition of Pd(0) to a B-B bond, see: Yang, F. Y.; Cheng, C. H. J. Am. Chem. Soc. 2001, 123, 761.
22. 2 is commercially available from Aldrich Chemical Company and, on scale, from BASF.
23. (a) See ref 7.
24. (b) Iverson, C. N.; Smith, M. R., III. Organometallics 1996, 15, 5155.
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26. For a review, see: (a) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346. For select examples of hydrogenation, see: (b) ven den Berg, M.; Minnard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539. (c) For examples of hydrosilation, see: Jensen, J. F.; Svendsen, B. Y.; la Cour, T. V.; Pedersen, H. L.; Johannsen, M. J. Am. Chem. Soc. 2002, 124, 4558. (d) For examples of hydroboration, see: Ma, M. F. P.; Li, K.; Zhou, Z.; Tang, C.; Chan. A. S. C. Tetrahedron: Asymmetry 1999, 10, 3259.
27. For a review, see: (a) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346. For select examples of hydrogenation, see: (b) ven den Berg, M.; Minnard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539. (c) For examples of hydrosilation, see: Jensen, J. F.; Svendsen, B. Y.; la Cour, T. V.; Pedersen, H. L.; Johannsen, M. J. Am. Chem. Soc. 2002, 124, 4558. (d) For examples of hydroboration, see: Ma, M. F. P.; Li, K.; Zhou, Z.; Tang, C.; Chan. A. S. C. Tetrahedron: Asymmetry 1999, 10, 3259.
28. For a review, see: (a) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346. For select examples of hydrogenation, see: (b) ven den Berg, M.; Minnard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539. (c) For examples of hydrosilation, see: Jensen, J. F.; Svendsen, B. Y.; la Cour, T. V.; Pedersen, H. L.; Johannsen, M. J. Am. Chem. Soc. 2002, 124, 4558. (d) For examples of hydroboration, see: Ma, M. F. P.; Li, K.; Zhou, Z.; Tang, C.; Chan. A. S. C. Tetrahedron: Asymmetry 1999, 10, 3259.
29. For a review, see: (a) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346. For select examples of hydrogenation, see: (b) ven den Berg, M.; Minnard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539. (c) For examples of hydrosilation, see: Jensen, J. F.; Svendsen, B. Y.; la Cour, T. V.; Pedersen, H. L.; Johannsen, M. J. Am. Chem. Soc. 2002, 124, 4558. (d) For examples of hydroboration, see: Ma, M. F. P.; Li, K.; Zhou, Z.; Tang, C.; Chan. A. S. C. Tetrahedron: Asymmetry 1999, 10, 3259.
30. Keller, E.; Maurer, J.; Naasz, R.; Schader, T.; Meetsma, A.; Feringa, B. L. Tetrahedron: Asymmetry 1998, 9, 2409.
31. Allenes were either commercially available (entry 5, Table 2) or conveniently prepared from terminal alkenes by cyclopropanation with dibromocarbene (Makosza, M.; Fedorynski, M. Synth. Commun. 1973, 3, 305) followed by treatment with Mg° (Xu, L.; Tao, F.; Yu, T. Tetrahedron Lett. 1985, 26, 4231).
32. Allenes were either commercially available (entry 5, Table 2) or conveniently prepared from terminal alkenes by cyclopropanation with dibromocarbene (Makosza, M.; Fedorynski, M. Synth. Commun. 1973, 3, 305) followed by treatment with Mg° (Xu, L.; Tao, F.; Yu, T. Tetrahedron Lett. 1985, 26, 4231).
33. The high level of chirality transfer for this reaction stands in stark contrast to that of reactions of analogous α-alkyl chiral allylboronates which lack the vinylic boronate group: Hoffmann, R. W. Pure Appl. Chem. 1988, 60, 123.