Vicinal amino alcohols as organocatalysts in asymmetric cross-aldol reaction of ketones: Application in the synthesis of convolutamydine A

Organic Letters

Volumn 9, Issue 26, 2007, Pages 5473-5476

  Malkov, Andrei V ^a   Kabeshov, Mikhail A ^a   Bella, Marco ^a,b   Kysilka, Ondřej ^a,c   Malyshev, Denis A ^a,d   Pluháčková, Kristýna ^a,e   Kočovský, Pavel ^a  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

^c INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

^d RUSSIAN ACADEMY OF SCIENCES   (Russian Federation)

^e CHARLES UNIVERSITY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 38349176362     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7023983     Document Type: Article

References (56)

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6. (d) For kinetic studies on the aldol reaction of acetophenone with acetone and related examples, see: Guthrie, J. P.; Wang, X.-P. Can. J. Chem. 1991, 69, 339 and references therein.
7. Amino alcohols and vicinal diamines have been previously shown to catalyze aldol-type reactions. For examples of the aldol reaction of aldehydes with α-fluoro-acetone, catalyzed by prolinol, see: (a) Zhong, G.; Fan, J.; Barbas, C. F. Tetrahedron Lett. 2004, 45, 5681. For Robinson annulation, catalyzed by prolinol and its congeners (though lacking the information on enantioselectivity), see:
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11. (e) Notz, W.; Tanaka, F.; Barbas, C. F. Acc. Chem. Res. 2004, 37, 580. The amino alcohols typically featured a secondary amine moiety, whereas the diamines typically contained a combination of one secondary and one tertiary amino group or one primary and one tertiary. For the use of amino acids with a primary amino group as catalysts for aldol reaction, see for example:
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20. 3j
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27. 2 produced only traces of (±)-2b in pure acetone.
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37. (a) Franz, A. K.; Dreyfuss, P. D.; Schreiber, S. L. J. Am. Chem. Soc. 2007, 129, 1020.
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40. 2COEt (88% ee).
41. 10a suggesting a partial racemization during the isolation process or that the natural product might not be enantiopure.
42. 2-hexane- methanol mixture provided enantiopure (R)-(+)-2c.
43. 9 can be attributed to dehydration-rehydration rather then the retroaldol-aldol sequence.
44. A slow conversion of lb into (±)-2b was observed with quinine as catalyst in pure acetone; the reaction was completed in 4 days.
45. 2.
46. 4c
47. The overall ee of the product (80% ee after 2 h) in this instance was a mathematical combination of the enantiopurity of the added (S)-(-)- 2b (20 mol% of 99% ee) and that normally produced on catalysis with leucinol (35% conversion, 70% ee).
48. For a discussion of another case of gradual amplification (operating via a different mechanism), see: Mathew, S. P.; Iwamura, H.; Blackmond, D. G. Angew. Chem., Int. Ed. 2004, 43, 3317 and references therein.
49. Pihko has observed an interesting increase in enantioselectivity in the proline-catalyzed aldehyde-ketone aldol reactions when triethylamine was added to the reaction mixture (Pihko, P. M.; Laurikainen, K. M.; Usano, A.; Nyberg, A. I.; Jatta, A.; Kaavi, J. A. Tetrahedron 2006, 62, 317); however, this effect does not appear to be related to our reactions.
50. 3a However, leucinol, being a primary amine, offers further stabilization of the transition state by an additional hydrogen bonding between the NH and OH, not available in the case of prolinol.
51. The reaction of the syn-enamine 4b (featuring in 6) appears to be the lowest-energy pathway. For a discussion of this effect, see ref 6b and Cheong, P. H. Y.; Zhang, H. L.; Thayumanavan, R.; Tanaka, F.; Houk, K. N.; Barbas, G F. Org. Lett. 2006, 8, 811.
52. 3 (X = F, Cl, MeO; Y = F, Cl) reacted with acetone in the presence of L-valinol as catalyst to afford the corresponding aldol products with 64-82% ee; details will be revealed in a full paper.
53. For the synthesis of racemic convolutamydine A, see ref 7c and the following: (a) Jnaneshwar, G. K.; Deshpande, V. H. J. Chem. Res., Synop. 1999, 632.
54. (b) Jnaneshwara, G. K.; Bedekar, A. V.; Deshpande, V. H. Synth. Commun. 1999, 29, 3627. For the synthesis of racemic convolutamydine C, see:
55. (c) Miah, S.; Moody, C. J.; Richards, I. C.; Slawin, A. M. Z. J. Chem. Soc., Perkin Trans. 1 1997, 2405. For the synthesis of both enantiomers of convolutamydine B and E using a stoichiometric chiral auxiliary, see:
56. (d) Nakamura, T.; Shirokawa, S.; Hosokawa, S.; Nakazaki, A.; Kobayashi, S. Org. Lett. 2006, 5, 677.