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Volumn 50, Issue 28, 2011, Pages 6370-6374

Palladium-mediated annulation of vinyl aziridines with michael acceptors: Stereocontrolled synthesis of substituted pyrrolidines and its application in a formal synthesis of (-)-α-kainic acid

Author keywords

annulation; aziridines; palladium; pyrrolidines; synthetic methods

Indexed keywords

ANNULATION; AZIRIDINES; DIASTEREO-SELECTIVITY; FORMAL SYNTHESIS; KAINIC ACID; METHYL VINYL KETONES; MICHAEL ACCEPTORS; PYRROLIDINES; STEREOCONTROLLED SYNTHESIS; SYNTHETIC METHODS; SYNTHETIC UTILITY;

EID: 79959748114     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201101389     Document Type: Article
Times cited : (110)

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    • Resubjection of a 93:7 mixture of 3 aA / 4 aA to the standard reaction conditions for 14 hours resulted in a final ratio of 96:4. Resubjection of a 24:76 mixture of 3 aA / 4 aA to the standard reaction conditions resulted in a final ratio of 23:77, even after extended reaction time (48 h). These results indicate that the reaction is essentially under kinetic control. We thank one of the reviewers for encouraging us to test whether the reaction was under kinetic or thermodynamic control.
    • Resubjection of a 93:7 mixture of 3 aA / 4 aA to the standard reaction conditions for 14 hours resulted in a final ratio of 96:4. Resubjection of a 24:76 mixture of 3 aA / 4 aA to the standard reaction conditions resulted in a final ratio of 23:77, even after extended reaction time (48 h). These results indicate that the reaction is essentially under kinetic control. We thank one of the reviewers for encouraging us to test whether the reaction was under kinetic or thermodynamic control.
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