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Volumn 47, Issue 45, 2008, Pages 8703-8706

Organocatalytic asymmetric aziridination of enones

Author keywords

Asymmetric catalysis; Aziridines; Domino reactions; Ketones; Organocatalysis

Indexed keywords

AMINES; CATALYSIS; ENANTIOSELECTIVITY; KETONES; REACTION KINETICS;

EID: 55249110210     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200803647     Document Type: Article
Times cited : (159)

References (47)
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    • For useful examples of the potential of chiral primary amines derived from cinchona alkaloids in iminium activation of enones, see: a J.-W. Xie, W. Chen, R. Li, M. Zeng, W. Du, L. Yue, Y.-C. Chen, Y. Wu, J. Zhu, J.-G. Deng, Angew. Chem. 2007, 119, 393;
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    • The results obtained by using the catalyst combination 1a or 9-amino(9-deoxy)epi-hydroquinine 2 in combination with different counteranions (trifluoroacetate, tosylate, benzoate) in the organocatalyzed aziridination did not bring any appreciable improvement in chemo- or stereoselectivity, confirming the superior efficiency of the catalyst salt 1b. Using the opposite enantiomeric counteranion 3 (L-N-Boc phenylglycine) afforded the same enantiomeric products 10 with lower reactivity and selectivity.
    • The results obtained by using the catalyst combination 1a or 9-amino(9-deoxy)epi-hydroquinine 2 in combination with different counteranions (trifluoroacetate, tosylate, benzoate) in the organocatalyzed aziridination did not bring any appreciable improvement in chemo- or stereoselectivity, confirming the superior efficiency of the catalyst salt 1b. Using the opposite enantiomeric counteranion 3 (L-N-Boc phenylglycine) afforded the same enantiomeric products 10 with lower reactivity and selectivity.
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    • For the use of a similar catalytic system in the highly enantioselective epoxidation of cyclic enones, see: a X. Wang, C. M. Reisinger, B. List, J. Am. Chem. Soc. 2008, 130, 6070
    • For the use of a similar catalytic system in the highly enantioselective epoxidation of cyclic enones, see: a) X. Wang, C. M. Reisinger, B. List, J. Am. Chem. Soc. 2008, 130, 6070.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.