Enantioselective addition of 2-(trimethylsilyloxy)furan to aldehydes using Cr(salen) as catalyst. Effect of water on enantioselectivity

Chemistry Letters

Volumn 32, Issue 7, 2003, Pages 584-585

  Matsuoka, Yuko ^a   Irie, Ryo ^a   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 (TRIMETHYLSILYLOXY)FURAN; ALDEHYDE; CHROMIUM; FURAN DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLOADDITION; ENANTIOSELECTIVITY; STEREOCHEMISTRY;

EID: 0141540720     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2003.584     Document Type: Article

References (26)

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12. This addition is a Mukaiyama aldol-like reaction with dienol silyl ether.
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14. Metallosalens possessing a binaphthyl unit are referred to as second-generation metallosalens: Y. N. Ito and T. Katsuki, Bull. Chem. Soc. Jpn., 72, 603 (1999).
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18. 1H NMR analysis, the protons at the carbinol carbons in the syn-products derived from octanal, cyclohexanecarboxaldehyde, and benzaldehyde have been reported to appear in ca. 0.1-0.3 ppm higher than the corresponding protons in the anti-products (Ref. 9). The relative configurations of the products derived from other aldehydes were tentatively assigned according to this report.
19. E. M. Carreira, in "Comprehensive Asymmetric Catalysis III," ed. by E. N. Jacobsen, A. Pfaltz, and H. Yamamoto, Springer, Berlin (1999), Vol. 29.1, p 997.
20. For the previous discussions of water effect on asymmetric Mukaiyama aldol reactions, see: a) M. Sodeoka, K. Ohrai, and M. Shibasaki, J. Org. Chem., 60, 2648 (1995). b) O. Fujimura, J. Am. Chem. Soc., 120, 10032 (1998). c) S. Kobayashi, S. Nagayama, and T. Busujima, Tetrahedron, 55, 8739 (1999). d) Y. Yamashita, H. Ishitani, H. Shimizu, and S. Kobayashi, J. Am. Chem. Soc., 124, 3292 (2002).
21. For the previous discussions of water effect on asymmetric Mukaiyama aldol reactions, see: a) M. Sodeoka, K. Ohrai, and M. Shibasaki, J. Org. Chem., 60, 2648 (1995). b) O. Fujimura, J. Am. Chem. Soc., 120, 10032 (1998). c) S. Kobayashi, S. Nagayama, and T. Busujima, Tetrahedron, 55, 8739 (1999). d) Y. Yamashita, H. Ishitani, H. Shimizu, and S. Kobayashi, J. Am. Chem. Soc., 124, 3292 (2002).
22. For the previous discussions of water effect on asymmetric Mukaiyama aldol reactions, see: a) M. Sodeoka, K. Ohrai, and M. Shibasaki, J. Org. Chem., 60, 2648 (1995). b) O. Fujimura, J. Am. Chem. Soc., 120, 10032 (1998). c) S. Kobayashi, S. Nagayama, and T. Busujima, Tetrahedron, 55, 8739 (1999). d) Y. Yamashita, H. Ishitani, H. Shimizu, and S. Kobayashi, J. Am. Chem. Soc., 124, 3292 (2002).
23. For the previous discussions of water effect on asymmetric Mukaiyama aldol reactions, see: a) M. Sodeoka, K. Ohrai, and M. Shibasaki, J. Org. Chem., 60, 2648 (1995). b) O. Fujimura, J. Am. Chem. Soc., 120, 10032 (1998). c) S. Kobayashi, S. Nagayama, and T. Busujima, Tetrahedron, 55, 8739 (1999). d) Y. Yamashita, H. Ishitani, H. Shimizu, and S. Kobayashi, J. Am. Chem. Soc., 124, 3292 (2002).
24. The effects of water might be manifold. We cannot rigorously exclude the possibility that water could prevent A from promoting the non-enantioselective reaction (Ref. 13 and 14c). Coordination of water and hydration of the counter anion would also change the catalyst structure as suggested by the reviewers. After this manuscript was submitted, however, secondary alcohols have been found to be effective as additives and enantiomeric alcohols to produce the same additive effect. Thus, the coordination of the hydroxylic ingredients to the catalyst is unlikely to be significant for the change of the stereochemical outcome. The utilities of alcoholic additives are currently under investigation.
25. The reaction with complex 2a in the absence of water did not proceed, but the reaction in the presence of water showed high enantioselectivity [54%, anti:syn = 41:59, 92% ee (anti) and 90% ee (syn), at -20°C].
26. 1H NMR (400 MHz) analysis. The enantiomeric excess of the resulting butenolides was determined as described in footnote b in Table 1.