188845-76-3

Upstream product

• 108448-77-7 (+)-camphorsultam 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 287117-69-5 (1R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carboxylic acid-(2-oxo-cyclohex-3-enyl)-amide 
• 287117-72-0 (1S,2R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carboxylic acid-(2-hydroxy-cyclohex-3-enyl)-amide 
• 108448-77-7 (+)-camphorsultam 

Relevant academic research and scientific papers

A formal asymmetric synthesis of (-)-epibatidine using a highly diastereoselective hetero Diels-Alder reaction

A formal asymmetric synthesis of (-)-epibatidine is reported. The key step of the synthesis is a regio- and diastereoselective cycloaddition of silyloxycyclohexadiene with the acylnitroso dienophite derived from (+)- camphorsultam. The resulting cycloadduct was readily transformed into the N- protected-7-azabicycto[2.2.1]heptan-2-one derivative which has previously been transformed into(-)-epibatidine. (C) 2000 Elsevier Science.

14. Origin of Diastereoselectivity in the Thermal [4+2] Cycloadditions of Dienophiles Derived from Oppolzer's Sultams: Steric vs. Stereoelectronic Influences

Comparative semi-empirical PM3 and ab initio STO 3-21G calculations on bornanesultam-derived dienophiles containing the structural moiety SO2-N-C(O)-X(α) = Y(β) suggest that, among the conformers of low energy, the thermodynamically less stable SO2/C(O)-syn,C(O)/X=Y-s-cis conformation is also reactive in terms of LUMO level and atomic coefficients, Furthermore, the X(α), Y(β) LUMO atomic coefficients are nonequivalent with respect to both X(α)-re and X(α)-si faces, and thus have, depending on the conformation, a matching or mismatching stereoelectronic influence with the co-operative steric effect. This dissymmetry is believed to result from the generalized anomeric effect of the N lone pair, itself anomerically stabilized and directed, in the absence of crucial steric interactions, by the pseudo-axial anti-periplanar S=O bond. Five N-acyl-substituted bornanesultams are discussed ((-)-1a: N-acryloyl, X=CH, Y=CH2; (-)-1b: N-crotonoyl, X=CH, Y=CHMe; (-)-1c: N,N'-fumaroyl, X=CH, Y=CH(C(O)-bornanesultam); 2a: N-glyoxyloyl, X=CH, Y=O; 2b: N-acylnitroso, X=N, Y=O). In this context, differences with toluenesultams 3 are pointed out. A previous report on N-(acylnitroso)-bornanesultam 2b is revisited, and the diastereoselectivity observed is shown to result from thermodynamic control.