Aqueous enantioselective organocatalytic Diels-Alder reactions employing hydrazide catalysts. A new scaffold for organic acceleration

Organic Letters

Volumn 7, Issue 19, 2005, Pages 4141-4144

  Lemay, Mathieu ^a   Ogilvie, William W ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 25444465184     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051476w     Document Type: Article

References (36)

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31. 1H 500 MHz NMR of the corresponding (+)-(R,R)-hydrobenzoin acetals. The absolute configurations of major products 4 and 6 were established by comparison to the NMR spectra of the (+)-(R,R)-hydrobenzoin acetals of (5)-4 and (5)-6 prepared independently (refs 3 and 10).
32. In contrast, acyclic hydrazides lacking substitution at this position are effective in an achiral sense. See ref 8.
33. An uncatalyzed reaction did not produce any detectable product after 24 h at 23°C. A reaction catalyzed by 0.2 equiv of acid gave a trace of product (<5%) after 24 h at 23°C, showing a slight preference for the endo product (1.3:1).
34. Enantiomeric excesses for endo isomers are given in Supporting Information.
35. 3,10
36. 3