Rhodium(II)-catalyzed aziridination of allyl-substituted sulfonamides and carbamates

Journal of Organic Chemistry

Volumn 69, Issue 19, 2004, Pages 6377-6386

  Padwa, Albert ^a   Flick, Andrew C ^a   Leverett, Carolyn A ^a   Stengel, Thomas ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; MAGNESIA; METHANOL; SULFONATION; X RAY CRYSTALLOGRAPHY;

AZIRIDINATION; IMINOIODINANE; SULFONAMIDES;

RHODIUM COMPOUNDS;

ALLYL COMPOUND; AMIDE; AMPHOLYTE; ANION; AZIRIDINE DERIVATIVE; BENZOFURAN DERIVATIVE; CARBAMIC ACID DERIVATIVE; CYCLOALKENE; INDOLE DERIVATIVE; IODINE; IODINE DERIVATIVE; MAGNESIUM OXIDE; METHANOL; REAGENT; RHODIUM; SULFONAMIDE;

ACYLATION; AMINATION; ARTICLE; AZIRIDINATION; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; REPRODUCIBILITY; RING OPENING; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS; TECHNIQUE; X RAY CRYSTALLOGRAPHY;

AZIRIDINES; CARBAMATES; CATALYSIS; MAGNETIC RESONANCE SPECTROSCOPY; RHODIUM; SULFONAMIDES;

EID: 4644238043     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048990k     Document Type: Article

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97. One of the reviewers has suggested an alternative mechanism involving addition of the nucleophile from the coordination sphere of the metal in 45 to give 41, 47, 48, and 49 directly, without the intermediacy of the dipolar species 46. Although this pathway is consistent with the observed syn-selectivity of addition, we believe that it can be discounted because one would expect acetate transfer in all cases, independent of other nucleophiles present.
98. Another reasonable possibility suggested by one of the reviewers is that the dipolar structures 56-58 might adopt different conformations, due to a buttressing effect of the tosyl group, and this may change the steric requirements around the carbon atom that is attacked by the nucleophile.
99. For structures 57 and 58, there is the possibility that the intermediate exists as a mixture of dipolar and aziridine structures, the dipolar one being responsible for the syn-addition product and the highly strained aziridine for the anti-addition product.
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101. 3, MeOH (70% yield) according to the procedure described in ref 35.
102. 3, MeOH (65% yield) according to the procedure described in ref 35.
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