Organocatalytic asymmetric michael addition of aldehydes to β-nitroacroleine dimethyl acetal

Organic Letters

Volumn 8, Issue 26, 2006, Pages 6135-6138

  Reyes, Efraim ^a   Vicario, Jose L ^a   Badía, Dolores ^a   Carrillo, Luisa ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

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Indexed keywords

EID: 33846126231     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062627d     Document Type: Article

References (47)

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36. MacMillan imidazolidinone catalysts were also tested in the reaction, but they did not show any catalytic activity.
37. The absolute configuration of 17a has been assigned by assuming a reaction pathway identical to that reported in the literature (ref 5). The relative configuration was established by comparison of NMR data.
38. To the best of our knowledge, this is the highest enantioselectivity reported for an organocatalytic reaction mediated by prolinol. For other prolinol-mediated reactions, see the following. Aldol reaction: (a) Mase, N.; Nakai, Y.; Ohara, N.; Yoda, H.; Takabe, K.; Tanaka, F.; Barbas, C. F., III. J. Am. Chem. Soc. 2006, 128, 734.
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47. Although the use of L-prolinol ethers 11 and 12 furnished a promising result in the initial experiments (Table 1), when we surveyed other solvents, we did not observe a significant inprovement in the enantio-and/or diastereoselectivity of the reaction.