Double Diastereoselection in Aldol Reactions Mediated by Dicyclohexylchloroborane between L-Erythrulose Derivatives and Chiral Aldehydes. The Felkin-Anh versus Cornforth Dichotomy

Journal of Organic Chemistry

Volumn 68, Issue 22, 2003, Pages 8577-8582

  Marco, J Alberto ^a   Carda, Miguel ^b   Díaz Oltra, Santiago ^b   Murga, Juan ^b   Falomir, Eva ^b   Roeper, Harald ^c  

^a UNIVERSITY OF VALENCIA   (Spain)

^b UNIVERSITAT JAUME I   (Spain)

^c Cargill R D Centre Europe   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; STEREOCHEMISTRY;

ALDOL REACTIONS;

ALDEHYDES;

ALDEHYDE; BORANE DERIVATIVE; DICYCLOHEXYLCHLOROBORANE; ERYTHRULOSE; FORMALDEHYDE; KETONE; KETOSE; SUGAR; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CHEMICAL REACTION; CHIRALITY; DIASTEREOISOMER; STEREOCHEMISTRY;

EID: 0142258961     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035159j     Document Type: Article

References (75)

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19. This stereochemical outcome of aldol reactions mediated by dicyclohexylboron chloride may be general in ketones bearing α-alkoxy or α-silyloxy substituents: Murga, J.; Falomir, E.; Carda, M.; González, F.; Marco, J. A. Org. Lett. 2001, 3, 901-904.
20. Other ketones structurally related to erythrulose behave in the same way: (a) Carda, M.; Murga, J.; Falomir, E.; González, F.; Marco, J. A. Tetrahedron: Asymmetry 2000, 11, 3211-3220.
21. (b) Carda, M.; González, F.; Sánchez, R.; Marco, J. A. Tetrahedron: Asymmetry 2002, 13, 1005-1010.
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24. All chiral aldehydes were prepared according to literature procedures. Aldehydes (R)-3a and (S)-3a: Roush, W. R.; Palkowitz, A. D.; Palmer, M. A: J. J. Org. Chem, 1987, 52, 316-318. Aldehyde (R)-3b: Meyers, A. I.; Babiak, K. A.; Campbell, A. J.; Comins, D. L.; Fleming, M. P.; Henning, R.; Heuschmann, M.; Hudspeth, J. P.; Kane, J. M.; Reider, P. J.; Roland, D. M.; Shimizu, K.; Tomioka, K.; Walkup, R. D. J. Am. Chem. Soc. 1983, 105, 5015-5024. Aldehyde (S)-3b: Nagaoka, H.; Kishi, Y. Tetrahedron 1981, 37, 3873-3888. Aldehydes (R) -4a and (S)-4a: Massad, S. K.; Hawkins, L. D.; Baker, D. C. J. Org. Chem. 1983, 48, 5180-5182. Aldehydes (R)-4b and (S)-4b: Ito, Y.; Kobayashi, Y.; Kawabata, T.; Takase, M.; Terashima, S. Tetrahedron 1989, 45, 5767-5790. Aldehyde (R)-4c: Ohgo, Y.; Yoshimura, J.; Kono, M.; Sato, T. Bull. Chem. Soc. Jpn. 1969, 42, 2957-2961. Aldehyde (S)-4c was prepared via Swern oxidation of (R)-1,2-di-O-benzylglycerol, obtained from L-ascorbic acid as described in: Mikkilineni, A. B.; Kumar, P.; Abushanab, E. J. Org. Chem. 1988, 53, 6005-6009.
25. All chiral aldehydes were prepared according to literature procedures. Aldehydes (R)-3a and (S)-3a: Roush, W. R.; Palkowitz, A. D.; Palmer, M. A: J. J. Org. Chem, 1987, 52, 316-318. Aldehyde (R)-3b: Meyers, A. I.; Babiak, K. A.; Campbell, A. J.; Comins, D. L.; Fleming, M. P.; Henning, R.; Heuschmann, M.; Hudspeth, J. P.; Kane, J. M.; Reider, P. J.; Roland, D. M.; Shimizu, K.; Tomioka, K.; Walkup, R. D. J. Am. Chem. Soc. 1983, 105, 5015-5024. Aldehyde (S)-3b: Nagaoka, H.; Kishi, Y. Tetrahedron 1981, 37, 3873-3888. Aldehydes (R) -4a and (S)-4a: Massad, S. K.; Hawkins, L. D.; Baker, D. C. J. Org. Chem. 1983, 48, 5180-5182. Aldehydes (R)-4b and (S)-4b: Ito, Y.; Kobayashi, Y.; Kawabata, T.; Takase, M.; Terashima, S. Tetrahedron 1989, 45, 5767-5790. Aldehyde (R)-4c: Ohgo, Y.; Yoshimura, J.; Kono, M.; Sato, T. Bull. Chem. Soc. Jpn. 1969, 42, 2957-2961. Aldehyde (S)-4c was prepared via Swern oxidation of (R)-1,2-di-O-benzylglycerol, obtained from L-ascorbic acid as described in: Mikkilineni, A. B.; Kumar, P.; Abushanab, E. J. Org. Chem. 1988, 53, 6005-6009.
26. All chiral aldehydes were prepared according to literature procedures. Aldehydes (R)-3a and (S)-3a: Roush, W. R.; Palkowitz, A. D.; Palmer, M. A: J. J. Org. Chem, 1987, 52, 316-318. Aldehyde (R)-3b: Meyers, A. I.; Babiak, K. A.; Campbell, A. J.; Comins, D. L.; Fleming, M. P.; Henning, R.; Heuschmann, M.; Hudspeth, J. P.; Kane, J. M.; Reider, P. J.; Roland, D. M.; Shimizu, K.; Tomioka, K.; Walkup, R. D. J. Am. Chem. Soc. 1983, 105, 5015-5024. Aldehyde (S)-3b: Nagaoka, H.; Kishi, Y. Tetrahedron 1981, 37, 3873-3888. Aldehydes (R) -4a and (S)-4a: Massad, S. K.; Hawkins, L. D.; Baker, D. C. J. Org. Chem. 1983, 48, 5180-5182. Aldehydes (R)-4b and (S)-4b: Ito, Y.; Kobayashi, Y.; Kawabata, T.; Takase, M.; Terashima, S. Tetrahedron 1989, 45, 5767-5790. Aldehyde (R)-4c: Ohgo, Y.; Yoshimura, J.; Kono, M.; Sato, T. Bull. Chem. Soc. Jpn. 1969, 42, 2957-2961. Aldehyde (S)-4c was prepared via Swern oxidation of (R)-1,2-di-O-benzylglycerol, obtained from L-ascorbic acid as described in: Mikkilineni, A. B.; Kumar, P.; Abushanab, E. J. Org. Chem. 1988, 53, 6005-6009.
27. All chiral aldehydes were prepared according to literature procedures. Aldehydes (R)-3a and (S)-3a: Roush, W. R.; Palkowitz, A. D.; Palmer, M. A: J. J. Org. Chem, 1987, 52, 316-318. Aldehyde (R)-3b: Meyers, A. I.; Babiak, K. A.; Campbell, A. J.; Comins, D. L.; Fleming, M. P.; Henning, R.; Heuschmann, M.; Hudspeth, J. P.; Kane, J. M.; Reider, P. J.; Roland, D. M.; Shimizu, K.; Tomioka, K.; Walkup, R. D. J. Am. Chem. Soc. 1983, 105, 5015-5024. Aldehyde (S)-3b: Nagaoka, H.; Kishi, Y. Tetrahedron 1981, 37, 3873-3888. Aldehydes (R) -4a and (S)-4a: Massad, S. K.; Hawkins, L. D.; Baker, D. C. J. Org. Chem. 1983, 48, 5180-5182. Aldehydes (R)-4b and (S)-4b: Ito, Y.; Kobayashi, Y.; Kawabata, T.; Takase, M.; Terashima, S. Tetrahedron 1989, 45, 5767-5790. Aldehyde (R)-4c: Ohgo, Y.; Yoshimura, J.; Kono, M.; Sato, T. Bull. Chem. Soc. Jpn. 1969, 42, 2957-2961. Aldehyde (S)-4c was prepared via Swern oxidation of (R)-1,2-di-O-benzylglycerol, obtained from L-ascorbic acid as described in: Mikkilineni, A. B.; Kumar, P.; Abushanab, E. J. Org. Chem. 1988, 53, 6005-6009.
28. All chiral aldehydes were prepared according to literature procedures. Aldehydes (R)-3a and (S)-3a: Roush, W. R.; Palkowitz, A. D.; Palmer, M. A: J. J. Org. Chem, 1987, 52, 316-318. Aldehyde (R)-3b: Meyers, A. I.; Babiak, K. A.; Campbell, A. J.; Comins, D. L.; Fleming, M. P.; Henning, R.; Heuschmann, M.; Hudspeth, J. P.; Kane, J. M.; Reider, P. J.; Roland, D. M.; Shimizu, K.; Tomioka, K.; Walkup, R. D. J. Am. Chem. Soc. 1983, 105, 5015-5024. Aldehyde (S)-3b: Nagaoka, H.; Kishi, Y. Tetrahedron 1981, 37, 3873-3888. Aldehydes (R) -4a and (S)-4a: Massad, S. K.; Hawkins, L. D.; Baker, D. C. J. Org. Chem. 1983, 48, 5180-5182. Aldehydes (R)-4b and (S)-4b: Ito, Y.; Kobayashi, Y.; Kawabata, T.; Takase, M.; Terashima, S. Tetrahedron 1989, 45, 5767-5790. Aldehyde (R)-4c: Ohgo, Y.; Yoshimura, J.; Kono, M.; Sato, T. Bull. Chem. Soc. Jpn. 1969, 42, 2957-2961. Aldehyde (S)-4c was prepared via Swern oxidation of (R)-1,2-di-O-benzylglycerol, obtained from L-ascorbic acid as described in: Mikkilineni, A. B.; Kumar, P.; Abushanab, E. J. Org. Chem. 1988, 53, 6005-6009.
29. All chiral aldehydes were prepared according to literature procedures. Aldehydes (R)-3a and (S)-3a: Roush, W. R.; Palkowitz, A. D.; Palmer, M. A: J. J. Org. Chem, 1987, 52, 316-318. Aldehyde (R)-3b: Meyers, A. I.; Babiak, K. A.; Campbell, A. J.; Comins, D. L.; Fleming, M. P.; Henning, R.; Heuschmann, M.; Hudspeth, J. P.; Kane, J. M.; Reider, P. J.; Roland, D. M.; Shimizu, K.; Tomioka, K.; Walkup, R. D. J. Am. Chem. Soc. 1983, 105, 5015-5024. Aldehyde (S)-3b: Nagaoka, H.; Kishi, Y. Tetrahedron 1981, 37, 3873-3888. Aldehydes (R) -4a and (S)-4a: Massad, S. K.; Hawkins, L. D.; Baker, D. C. J. Org. Chem. 1983, 48, 5180-5182. Aldehydes (R)-4b and (S)-4b: Ito, Y.; Kobayashi, Y.; Kawabata, T.; Takase, M.; Terashima, S. Tetrahedron 1989, 45, 5767-5790. Aldehyde (R)-4c: Ohgo, Y.; Yoshimura, J.; Kono, M.; Sato, T. Bull. Chem. Soc. Jpn. 1969, 42, 2957-2961. Aldehyde (S)-4c was prepared via Swern oxidation of (R)-1,2-di-O-benzylglycerol, obtained from L-ascorbic acid as described in: Mikkilineni, A. B.; Kumar, P.; Abushanab, E. J. Org. Chem. 1988, 53, 6005-6009.
30. All chiral aldehydes were prepared according to literature procedures. Aldehydes (R)-3a and (S)-3a: Roush, W. R.; Palkowitz, A. D.; Palmer, M. A: J. J. Org. Chem, 1987, 52, 316-318. Aldehyde (R)-3b: Meyers, A. I.; Babiak, K. A.; Campbell, A. J.; Comins, D. L.; Fleming, M. P.; Henning, R.; Heuschmann, M.; Hudspeth, J. P.; Kane, J. M.; Reider, P. J.; Roland, D. M.; Shimizu, K.; Tomioka, K.; Walkup, R. D. J. Am. Chem. Soc. 1983, 105, 5015-5024. Aldehyde (S)-3b: Nagaoka, H.; Kishi, Y. Tetrahedron 1981, 37, 3873-3888. Aldehydes (R) -4a and (S)-4a: Massad, S. K.; Hawkins, L. D.; Baker, D. C. J. Org. Chem. 1983, 48, 5180-5182. Aldehydes (R)-4b and (S)-4b: Ito, Y.; Kobayashi, Y.; Kawabata, T.; Takase, M.; Terashima, S. Tetrahedron 1989, 45, 5767-5790. Aldehyde (R)-4c: Ohgo, Y.; Yoshimura, J.; Kono, M.; Sato, T. Bull. Chem. Soc. Jpn. 1969, 42, 2957-2961. Aldehyde (S)-4c was prepared via Swern oxidation of (R)-1,2-di-O-benzylglycerol, obtained from L-ascorbic acid as described in: Mikkilineni, A. B.; Kumar, P.; Abushanab, E. J. Org. Chem. 1988, 53, 6005-6009.
31. (a) The aldol reactions were also made with aldehydes bearing a TBS protecting group. The results were identical with those of TPS protected aldehydes.
32. 4 to yield the expected syn-1,3-diols.10 These were subsequently converted into acetonides, which were then studied by means of NMR.11 Standard manipulations of the protecting groups further permitted the preparation of other cyclic derivatives suitable for similar NMR studies. Descriptions of these chemical correlations and analytical data for the correlation products are given in the Supporting Information.
33. The stereostructure of compound 6a was established by means of an X-ray diffraction analysis. Crystallographic data (excluding structure factors) have been deposited at the Cambridge Crystallographic Data Center as Supporting Information with reference CCDC-210749. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK [fax +44(0)-1223-336033 or e-mail deposit@ccdc.cam.ac.uk].
34. Paterson, I.; Channon, J. A. Tetrahedron Lett. 1992, 33, 797-800.
35. Rychnovsky, S. D.; Rogers, B. N.; Richardson, T. I. Acc. Chem. Res. 1998, 31, 9-17.
36. Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920-1923.
37. For theoretical studies on boron aldol reactions, see: (a) Li, Y.; Paddon-Row, M. N.; Houk, K. N. J. Org. Chem. 1990, 55, 481-493.
38. (b) Goodman, J. M.; Kahn, S. D.; Paterson, I. J. Org. Chem. 1990, 55, 3295-3303.
39. (c) Bernardi, A.; Capelli, A. M.; Gennari, C.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1990, 55, 3576-3581.
40. (d) Bernardi, A.; Capelli, A. M.; Comotti, A.; Gennari, C.; Gardner, M.; Goodman, J. M.; Paterson, I. Tetrahedron 1991, 47, 3471-3484.
41. (e) Bernardi, F.; Robb, M. A.; Suzzi-Valli, G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem. 1991, 56, 6472-6475.
42. (f) Gennari, C.; Vieth, S.; Comotti, A.; Vulpetti, A.; Goodman, J. M.; Paterson, I. Tetrahedron 1992, 48, 4439-4458.
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44. Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499-2506. For another example that shows the importance of dipole alignment in aldol TSs, see: Boeckman, R. K., Jr.; Connell, B. T. J. Am. Chem. Soc. 1995, 117, 12368-12369.
45. Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499-2506. For another example that shows the importance of dipole alignment in aldol TSs, see: Boeckman, R. K., Jr.; Connell, B. T. J. Am. Chem. Soc. 1995, 117, 12368-12369.
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49. Roush, W. R. J. Org. Chem. 1991, 56, 4151-4157.
50. For a lucid analysis of the various factors which may influence the stereochemical outcome of aldol reactions, see: Lee, C. B.; Wu, Z.; Zhang, F.; Chappell, M. D.; Stachel, S. J.; Chou, T.-C.; Guan, Y.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123, 5249-5259.
51. Lodge, E. P.; Heathcock, C. H. J. Am. Chem. Soc. 1987, 109, 3353-3361. The "non-Anh" label refers to transition structures in which attack takes place anti to a substituent that neither has the lowest lying σ*C-X orbital (for α-heteroatom-substituted aldehydes) nor is the sterically bulkiest one (for aldehydes not bearing α-heteroatoms). See also ref 16.
52. Effects of β-protecting groups at either the enolate or the aldehyde on the degree of diastereoselectivity of aldol reactions have been previously described. In some cases, such effects were attributed to various origins (chelation, conformational effects, etc.) while in others they remained unexplained. See, for example: (a) Paterson, I.; Bower, S.; Tillyer, R. D. Tetrahedron Lett. 1993, 34, 4393-4396.
53. (b) Evans, D. A.; Calter, M. A. Tetrahedron Lett. 1993, 34, 6871-6874.
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56. (e) Roush, W. R.; Dilley, G. J. Tetrahedron Lett. 1999, 40, 4955-4959. Sometimes, influence of still more remote protecting groups has been observed: Roush, W. R.; Bannister, T. D.; Wendt, M. D. Tetrahedron Lett. 1993, 34, 8387-8390.
57. (e) Roush, W. R.; Dilley, G. J. Tetrahedron Lett. 1999, 40, 4955-4959. Sometimes, influence of still more remote protecting groups has been observed: Roush, W. R.; Bannister, T. D.; Wendt, M. D. Tetrahedron Lett. 1993, 34, 8387-8390.
58. This was established upon examination of NMR data for the crude aldol mixtures. In view of this synthetically useless result, we did not attempt to isolate individual compounds.
59. Provided that chelation is not involved in the transition state, achiral enolates react with α-oxygenated aldehydes to yield predominantly, albeit with variable diastereoselectivity, the Felkin aldols. See refs 1 and 2. For more recent cases, see, for example: (a) Esteve, C.; Ferrerò, M.; Romea, P.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1999, 40, 5079-5082.
60. (b) Lu, L.; Chang, H.-Y.; Fang, J.-M. J. Org. Chem. 1999, 64, 843-853. However, it is worth noting that Felkin aldols have been found to predominate in some reactions where chelation is likely to occur: Grandel, R.; Kazmaier, U. ; Rominger, F. J. Org. Chem. 1998, 63, 4524-4528.
61. (b) Lu, L.; Chang, H.-Y.; Fang, J.-M. J. Org. Chem. 1999, 64, 843-853. However, it is worth noting that Felkin aldols have been found to predominate in some reactions where chelation is likely to occur: Grandel, R.; Kazmaier, U. ; Rominger, F. J. Org. Chem. 1998, 63, 4524-4528.
62. For nucleophilic additions to aldehydes bearing α-heteroatoms other than oxygen, see, for example: (a) Reetz, M. T. Chem. Rev. 1999, 99, 1121-1162 (α-amino aldehydes).
63. (b) Enders, D.; Piva, O.; Burkamp, F. Tetrahedron 1996, 52, 2893-2908 (α-sulfenyl aldehydes).
64. (c) Enders, D.; Adam, J.; Klein, D.; Otten, T. Synlett 2000, 1371-1384 (α-silyl aldehydes). See also: Enders, D.; Burkamp, F. Collect. Czech. Chem. Commun. 2003, 68, 975-1006.
65. (c) Enders, D.; Adam, J.; Klein, D.; Otten, T. Synlett 2000, 1371-1384 (α-silyl aldehydes). See also: Enders, D.; Burkamp, F. Collect. Czech. Chem. Commun. 2003, 68, 975-1006.
66. Evans, D. A.; Siska, S. J.; Cee, V. J. Angew. Chem., Int. Ed. 2003, 42, 1761-1765.
67. Cornforth, J. W.; Cornforth, R. H.; Mathew, K. K. J. Chem. Soc. 1959, 112-127. See also: Paddon-Row, M. N.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 7162-7166.
68. Cornforth, J. W.; Cornforth, R. H.; Mathew, K. K. J. Chem. Soc. 1959, 112-127. See also: Paddon-Row, M. N.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 7162-7166.
69. The Cornforth model, as an alternative to the Felkin-Anh model, has already been proposed to explain the stereochemical outcome of additions of allylboranes to α-heteroatom-substituted aldehydes. See: Brinkmann, H.; Hoffmann, R. W. Chem. Ber. 1990, 123, 2395-2401 and references therein.
70. Doubly diastereoselective aldol reactions of chiral enolates with chiral α-oxygenated aldehydes are not extensively documented in the literature. Matched and mismatched processes have been reported, with the full range from total stereocontrol by the enolate to complete dominance of the aldehyde being observed. See refs 1 and 2 and, for more recent cases: (a) Nicolaou, K. C.; Piscopio, A. D.; Bertinato, P.; Chakraborty, T. K.; Minowa, N.; Koide, K. Chem. Eur. J. 1995, 1, 318-333.
71. (b) Kobayashi, S.; Furuta, T. Tetrahedron 1998, 54, 10275-10294.
72. (c) Esteve, C.; Ferrerò, M.; Romea, P.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1999, 40, 5083-5086.
73. (d) Nicolaou, K. C.; Pihko, P. M.; Diedrichs, N.; Zou, N.; Bernal, F. Angew. Chem., Int. Ed. 2001, 40, 1262-1265.
74. (e) Forsyth, C. J.; Hao, J.; Aiguade, J. Angew. Chem., Int. Ed. 2001, 40, 3663-3667.
75. Excluded from this discussion are chiral enolates in which the chirality resides in the ligands bound to the heteroatom. In these cases, stereocontrol by the chiral auxiliary is usually observed. See, for example: Gennari, C.; Pain, G.; Moresca, D. J. Chem. Org. 1995, 60, 6248-6249.