Catalytic desymmetrizing intramolecular Heck reaction: Evidence for an unusual hydroxy-directed migratory insertion

Angewandte Chemie - International Edition

Volumn 44, Issue 1, 2004, Pages 149-152

  Oestreich, Martin ^a   Sempere Culler, Fernando ^a   Machotta, Axel B ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

Asymmetric catalysis; Asymmetric synthesis; C C coupling; Palladium

Indexed keywords

HYDROXYL RADICAL; RADICAL; STYRENE;

ALLYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLIZATION; DIASTEREOISOMER; ENANTIOMER; HECK REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; RADICAL REACTION; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 11244311586     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460921     Document Type: Article

References (34)

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10. For the desymmetrization of bicyclodienes, see: M. Lautens, V. Zunic, Can. J. Chem. 2004, 82, 399-407.
11. For a different desymmetrization strategy for a cyclic substrate, see: S. Bräse, Synlett 1999, 1654-1656.
12. For a review of enantioselective desymmetrization, see: M. C. Willis, J. Chem. Soc. Perkin Trans, 1 1999, 1765-1784.
13. For other chelate-controlled Heck reactions, see: a) P. Nilsson, M. Larhed, A. Hallberg, J. Am. Chem. Soc. 2001, 123, 8217-8225; b) K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, J.-i. Yoshida, J. Am. Chem. Soc. 2001, 123, 11 577-11 585; c) P. Nilsson, M. Larhed, A. Hallberg, J. Am. Chem. Soc. 2003, 125, 3430-3431; d) for regioselective vinylation of allylic alcohols, see: E. Bernocchi, S. Cacci, P. G. Ciattini, E. Morera, G. Ortar, Tetrahedron Lett 1992, 33, 3073-3076.
14. For other chelate-controlled Heck reactions, see: a) P. Nilsson, M. Larhed, A. Hallberg, J. Am. Chem. Soc. 2001, 123, 8217-8225; b) K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, J.-i. Yoshida, J. Am. Chem. Soc. 2001, 123, 11577-11585; c) P. Nilsson, M. Larhed, A. Hallberg, J. Am. Chem. Soc. 2003, 125, 3430-3431; d) for regioselective vinylation of allylic alcohols, see: E. Bernocchi, S. Cacci, P. G. Ciattini, E. Morera, G. Ortar, Tetrahedron Lett 1992, 33, 3073-3076.
15. For other chelate-controlled Heck reactions, see: a) P. Nilsson, M. Larhed, A. Hallberg, J. Am. Chem. Soc. 2001, 123, 8217-8225; b) K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, J.-i. Yoshida, J. Am. Chem. Soc. 2001, 123, 11577-11585; c) P. Nilsson, M. Larhed, A. Hallberg, J. Am. Chem. Soc. 2003, 125, 3430-3431; d) for regioselective vinylation of allylic alcohols, see: E. Bernocchi, S. Cacci, P. G. Ciattini, E. Morera, G. Ortar, Tetrahedron Lett 1992, 33, 3073-3076.
16. For other chelate-controlled Heck reactions, see: a) P. Nilsson, M. Larhed, A. Hallberg, J. Am. Chem. Soc. 2001, 123, 8217-8225; b) K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, J.-i. Yoshida, J. Am. Chem. Soc. 2001, 123, 11577-11585; c) P. Nilsson, M. Larhed, A. Hallberg, J. Am. Chem. Soc. 2003, 125, 3430-3431; d) for regioselective vinylation of allylic alcohols, see: E. Bernocchi, S. Cacci, P. G. Ciattini, E. Morera, G. Ortar, Tetrahedron Lett 1992, 33, 3073-3076.
17. As a result of alkene migration, formation of two isomers was yet another issue. Nevertheless, identical enantiomeric excesses were measured for both isomers.
18. M. Oestreich, F. Sempere-Culler, Chem. Commun. 2004, 692-693, and references therein.
19. 2 precatalyst and 1.5 mol% L1 did not affect the enantioselectivity of the reaction.
20. The absolute configuration of 14 has not been determined yet since all attempts to derivatize and crystallize or chemically correlate 14 have failed so far.
21. C. Laue, G. Schröder, D. Arlt (Bayer AG), DE-A1 19522293, 1995.
22. Asymmetric Heck reactions using MeO-biphep have been reported: a) G. Trabesinger, A. Albinati, N. Feiken, R. W. Kunz, P. S. Pregosin, M. Tschoerner, J. Am. Chem. Soc. 1997, 119, 6315-6323; b) M. Tschoerner, A. Albinati, P. S. Pregosin, Organometallics 1999, 18, 670-678; c) L. F. Tietze, K. Thede, R. Schimpf, F. Sannicolò, Chem. Commun. 2000, 583-584.
23. Asymmetric Heck reactions using MeO-biphep have been reported: a) G. Trabesinger, A. Albinati, N. Feiken, R. W. Kunz, P. S. Pregosin, M. Tschoerner, J. Am. Chem. Soc. 1997, 119, 6315-6323; b) M. Tschoerner, A. Albinati, P. S. Pregosin, Organometallics 1999, 18, 670-678; c) L. F. Tietze, K. Thede, R. Schimpf, F. Sannicolò, Chem. Commun. 2000, 583-584.
24. Asymmetric Heck reactions using MeO-biphep have been reported: a) G. Trabesinger, A. Albinati, N. Feiken, R. W. Kunz, P. S. Pregosin, M. Tschoerner, J. Am. Chem. Soc. 1997, 119, 6315-6323; b) M. Tschoerner, A. Albinati, P. S. Pregosin, Organometallics 1999, 18, 670-678; c) L. F. Tietze, K. Thede, R. Schimpf, F. Sannicolò, Chem. Commun. 2000, 583-584.
25. A brief survey of oxazoline-containing P,N ligands showed that axially chiral diphosphines were the optimal choice for this intramolecular Heck reaction. For successful applications of P,N ligands, see: a) D. Kiely, P. J. Guiry, Tetrahedron Lett. 2002, 43, 9545-9547; b) L. Ripa, A. Hallberg, J. Org. Chem. 1997, 62, 595-602; c) For a review on P,N-ligands, see: O. Loiseleur, M. Hayashi, M. Keenan, N. Schmess, A. Pfaltz, J. Organomet. Chem. 1999, 576, 16-22.
26. A brief survey of oxazoline-containing P,N ligands showed that axially chiral diphosphines were the optimal choice for this intramolecular Heck reaction. For successful applications of P,N ligands, see: a) D. Kiely, P. J. Guiry, Tetrahedron Lett. 2002, 43, 9545-9547; b) L. Ripa, A. Hallberg, J. Org. Chem. 1997, 62, 595-602; c) For a review on P,N-ligands, see: O. Loiseleur, M. Hayashi, M. Keenan, N. Schmess, A. Pfaltz, J. Organomet. Chem. 1999, 576, 16-22.
27. A brief survey of oxazoline-containing P,N ligands showed that axially chiral diphosphines were the optimal choice for this intramolecular Heck reaction. For successful applications of P,N ligands, see: a) D. Kiely, P. J. Guiry, Tetrahedron Lett. 2002, 43, 9545-9547; b) L. Ripa, A. Hallberg, J. Org. Chem. 1997, 62, 595-602; c) For a review on P,N-ligands, see: O. Loiseleur, M. Hayashi, M. Keenan, N. Schmess, A. Pfaltz, J. Organomet. Chem. 1999, 576, 16-22.
28. 3B-promoted C-allylation of 2-hydroxyacetophenone with cinnamic alcohol followed by deoxygenation: Y. Horino, M. Naito, M. Kimura, S. Tanaka, Y. Tamaru, Tetrahedron Lett. 2001, 42, 3113-3116.
29. It should be noted that Shibasaki et al. employed tBuOH as a cosolvent in an asymmetric Heck reaction in order to suppress oxidation of a secondary-alcohol-containing substrate without affecting the level of enantioselectivity: K. Kondo, M. Sodeoka, M. Mori, M. Shibasaki, Synthesis 1993, 920-930. For a general overview on alcohols as cosolvents, see ref. [3b].
30. For an excellent review on substrate-directed reactions, see: A. H. Hoveyda, D. A. Evans, G. C. Fu, Chem. Rev. 1993, 93, 1307-1370.
31. A. Ashimori, B. Bachand, M. A. Calter, S. P. Govek, L. E. Overman, D. J. Poon, J. Am. Chem. Soc. 1998, 120, 6488-6499.
32. However, Wolfe et al. have recently presented evidence for an alkene insertion into an arylpalladium alkoxide intermediate: J. P. Wolfe, M. A. Rossi, J. Am. Chem. Soc. 2004, 126, 1620-1621.
33. In contrast, intramolecular coordination in the cyclization of 11 would require formation of a virtually planar (and strained) five-membered ring, which could potentially account for the distinctly diminished enantioselectivity.
34. M. Oestreich, F. Sempere-Culler, manuscript in preparation.