(-)-10,2-Camphorsultam TCI C1325

Chemical Identity

Other names: (2R)-Bornane-10,2-sultam · (1S,5R)-10,10-Dimethyl-3-thia-4-azatricyclo[5.2.1.0(1,5)]decane 3,3-Dioxide
CAS No.: 94594-90-8
Formula: C10H17NO2S
Molecular weight: 215.31 g/mol
Purity: >98.0%(GC)

Full identifiers (IUPAC, SMILES, InChIKey)

IUPAC: 10,10-dimethyl-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane 3,3-dioxide
SMILES: CC1(C2CCC13CS(=O)(=O)NC3C2)C
InChIKey: DPJYJNYYDJOJNO-UHFFFAOYSA-N
MDL: MDL00066271
PubChem: CID 145454

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TCI C1325 (-)-10,2-Camphorsultam, widely known as Oppolzer's sultam, is a classic chiral auxiliary built on the rigid camphor framework. Substrates are attached to the sultam nitrogen, transformed with high facial selectivity, and then released once the new stereocentre is set. It performs reliably in enolate alkylation, aldol reactions, Diels-Alder cycloadditions, and conjugate additions, and its crystalline derivatives often allow diastereomer purification. AMI Scientific supplies this TCI product in 1 g and 5 g packs, best stored cool, dry, and tightly closed.

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Baciocchi et al. (1994). Stereoselective Heteroaromatic Homolytic Substitution with Carbon Radicals Derived from Oppolzer's Camphorsultam. Synlett doi:10.1055/s-1994-23016
(1990). (−)-D-2,10-CAMPHORSULTAM. Organic Syntheses doi:10.15227/orgsyn.069.0154
Zhang et al. (2019). Asymmetric Difluoromethylthiolation of Carbon Nucleophiles with Optically Pure Difluoromethylthiolating Reagents Derived from Camphorsultam. Chinese Journal of Chemistry doi:10.1002/cjoc.201900298

References were compiled automatically from Crossref and every DOI was verified to exist. AMI Scientific is not affiliated with the authors or the publishers.