Stereochemical Models for Rh-Catalyzed Amination Reactions of Chiral Sulfamates

Organic Letters

Volumn 5, Issue 25, 2003, Pages 4823-4826

  Wehn, Paul M ^a   Lee, Jihee ^a   Du Bois, J ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; AZIRIDINE DERIVATIVE; CARBOXYLIC ACID; CHEMICAL AGENT; ESTER DERIVATIVE; MAGNESIUM OXIDE; RHODIUM; SULFUR DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODEL; CHIRALITY; DIASTEREOISOMER; OXIDATION; STEREOCHEMISTRY;

AMINATION; CATALYSIS; ESTERS; MOLECULAR STRUCTURE; RHODIUM; STEREOISOMERISM; SULFONIC ACIDS;

EID: 0345791433     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035776u     Document Type: Article

References (29)

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19. For Rh-catalyzed intramolecular aziridination using sulfonamides, see: Liang, J.-L.; Yuan, S.-X.; Chan, P. W. H.; Che, C.-M. Org. Lett. 2002, 4, 4507-4510. Using carbamates, see: (a) Padwa, A.; Stengel, T. Org. Lett. 2002, 4, 2137-2139. (b) Levites-Agababa, E.; Menhaji, E.; Perlson, L. N.; Rojas, C. M. Org. Lett. 2002, 4, 863-865.
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22. Intramolecular Cu-catalyzed aziridination with sulfamate and sulfonamide substrates has been described; see: (a) Duran, F.; Leman, L.; Ghini, A.; Burton, G.; Dauban, P.; Dodd, R. H. Org. Lett. 2002, 4, 2481-2483. (b) Dauban, P.; Sanière, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707-7708.
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29. We have observed that the catalyst structure can influence product diastereoselectivity in both insertion and animation reactions. Such findings suggest that the catalyst is involved in the product-forming step. A more detailed picture of the reactive substrate-catalyst complex is thus needed to account for quantitative differences in selectivity recorded for these processes.