New options for the reactivity of the burgess reagent with epoxides in both racemic and chiral auxiliary modes - Structural and mechanistic revisions, computational studies, and application to synthesis

European Journal of Organic Chemistry

Volumn , Issue 17, 2009, Pages 2806-2819

  Leisch, Hannes ^a   Sullivan, Bradford ^a   Fonovic, Branden ^a   Dudding, Travis ^a   Hudlicky, Tomas ^a  

^a BROCK UNIVERSITY   (Canada)

Author keywords

Amino alcohol derivatives; Balanol; Burgess reagent; Chiral auxiliaries; Density functional calculations; Enantioselectivity; Structure revisions; Sulfamidate synthesis

Indexed keywords

EID: 66449125307     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900159     Document Type: Article

References (64)

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55. See Supporting Information for calculated transition states. Owing to their higher activation barrier subsequent steps along this pathway were not considered.
56. Although even this reaction barrier is slightly too high, it was by far the lowest out of all the mechanistic possibilities considered.
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60. b) Wiberg bond indices for pertinent bond forming/breaking distances during 5-mem-TSl: C-N: 0.1588, C...O: 0.3007, and O....S: 0.4358.
61. An Intrinsic Reaction Coordinate (IRC) calculation confirmed that cis-5-mem sulfamidate was the immediate product of 5-mem-TSl.
62. See Supporting Information for details regarding these searches.
63. Multiple attempts were made to locate 5-mem-TSl in the presence of an epoxide bound Lewis acid, none of these attempts were successful in locating energetically feasible transition states.
64. For example a. reaction dynamic involving Brønsted acidic trimethylanimonium (a likely degradation product of Burgess reagent) was computed, and shown to have a reduced barrier to cyclohexene oxide ring opening as compared with that of the uncatalyzed processes (i.e. 5-mem-TSl).