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Cited by 14 publications
(3 citation statements)
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“…It shows that a retro-Claisen cleavage occurs during the reaction and then aminolysis between the intermediate and aminopyridine affords the product. 6 In the IR spectrum of 2, the band of ν N-H is at 3421 cm -1 compared with 3242 cm -1 of 1. This suggests that the N-H group of the amide is involved in hydrogen bonding in its solid state structure.…”
mentioning
confidence: 91%
“…It shows that a retro-Claisen cleavage occurs during the reaction and then aminolysis between the intermediate and aminopyridine affords the product. 6 In the IR spectrum of 2, the band of ν N-H is at 3421 cm -1 compared with 3242 cm -1 of 1. This suggests that the N-H group of the amide is involved in hydrogen bonding in its solid state structure.…”
mentioning
confidence: 91%
“…Since the targeted structure was a β-keto ester, the addition of 91 to 92 formally represented a Claisen condensation. The creation of fully substituted Claisen adducts (where deprotonation of the β-keto ester product is not feasible) is unusual, as are examples of stereoselective Claisen condensations. , We selected β-lactones as the acyl donor with the expectation that strain release would preclude the retro-Claisen pathway. An open question at the outset was the degree to which the stereogenic center in the β-lactone would impact the emerging fully substituted stereocenter.…”
Section: Resultsmentioning
confidence: 99%
“…An attempt to get any product by uncatalyzed reaction of DR19 with GMA was unsuccessful, even at 80 C and with reaction times of 48 h. The reaction was then tested with various catalysts, such as BFEt [42], TiBuO [43], ETPP [44], DMAP [45].…”
Section: Preparation and Characterization Of Ma19mentioning
confidence: 99%