Highly enantioenriched propargylic alcohols by oxazaborolidine-mediated reduction of acetylenic ketones

Journal of Organic Chemistry

Volumn 61, Issue 25, 1996, Pages 9021-9025

  Bach, Jordi ^a   Berenguer, Ramon ^a   Garcia, Jordi ^a   Loscertales, Teresa ^a   Vilarrasa, Jaume ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000846718     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9612943     Document Type: Article

References (70)

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44. Morita et al. have recently reported the reduction of an acetylenic ketone catalyzed by proline-derived oxazaborolidine [(S)-6, R = Me and Bu] in low yields and enantioselectivity: Morita, S.; Otsubo, K.; Matsubara, J.; Ohtani, T.; Uchida, M. Tetrahedron: Asymmetry 1995, 6, 245.
45. See also ref 2c. During the preparation of this manuscript a Note has appeared reporting the efficient reduction of a few acetylenic ketones with an excess of (S)-6 (R = Me) at -30 °C: Parker, K. A.; Ledeboer, M. W. J. Org. Chem. 1996, 61, 3214.
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54. Reactions were monitored by TLC. Triple-bond hydroboration byproducts were not detected. Temperature appeared to be crucial: an attempt to reduce 10a at rt lead to a complex mixture of products, whereas reduction at -40 °C was much slower and gave alcohol 12a in lower yield and stereoselectivity (64, 39 ee.).
55. In this connection it is timely to point out that, in our hands, reduction of 10c with neat (-)-DIP-Chloride at rt yielded a 70 of alcohol (-)-12c (97 ee.) after 2 days. The R configuration was assumed for the resulting alcohol in agreement with the mechanism accepted for such reductions.
56. t) was subjected to identical reduction conditions, with parallel results: 97 ee and 93 ee (using 1 equiv and 0.2 equiv of (R)-7, respectively).
57. (a) Compound 14a: Jeong K.-S.; Sjö, P.; Sharpless, K. B. Tetrahedron Lett. 1992, 33, 3833.
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63. Quallich, G. J.; Woodall, T. M. Tetrahedron Lett. 1993, 34, 4145. Its enantioraer, (LR, 2S)-2-amino-l, 2-diphenylethanol, is also commercially available.
64. By contrast, oxazaborolidine 9 showed a less satisfactory performance in the reduction of noncomplexed acetylenic ketones (74 yield, 69 ee, for ketone lOa). In the same way, reduction of 10a with catecholborane in the presence of (R)-6 at -57 °C showed an acceptable yield but a moderate selectivity (82 yield, 81 ee).
65. 3N (a good Lewis base) but not by the excess of borane present in the reaction mixture. (Figure Presented)
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69. A less detailed procedure (not optimized) can be found in ref 10b.
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