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    139628-16-3

    Catalog No. EBD2321614

    CAS 139628-16-3

    Name (4aR,7R,8aS)-8,8-dichloro-9,9-dimethyltetrahydro-4H-4a,7-methanobenzo[c][1,2]oxazireno[2,3-b]isothiazole 3,3-dioxide

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    Basic Information

    Molecular Formula: C10H13Cl2NO3S

    Molecular Weight: 298.19

    MDL Number: MFCD17214220

    Categories: Synthetic Chemistry > Basic Synthetic Reagents > Chiral Auxiliaries and Resolution Reagents Synthetic Chemistry > Organic Building Blocks > Other Organic Building Blocks

    Product Description:
    (-)-8,8-Dichlorocamphorsultam is a chiral auxiliary derived from camphorsulfonic acid. It is a white to off-white crystalline solid with a molecular formula of C10H13Cl2NO3S. The compound features a rigid, bicyclic camphor skeleton with a sulfonamide (sultam) group, which provides a well-defined chiral environment for asymmetric synthesis. Its primary and most significant application is as a highly effective chiral auxiliary in organic synthesis, particularly in enantioselective alkylation, aldol, and Diels-Alder reactions. The auxiliary is typically attached to a substrate (e.g., as an enolate equivalent) to induce diastereoselectivity during a key bond-forming step. After the desired transformation, the auxiliary can be cleaved under mild conditions to yield enantiomerically enriched products. It is a valuable tool for the preparation of chiral building blocks in pharmaceutical and fine chemical research. While not a commodity chemical, (-)-8,8-dichlorocamphorsultam is a specialized reagent available from suppliers of advanced synthetic and chiral chemicals. Its use is confined to laboratory-scale asymmetric methodology development and the synthesis of complex target molecules requiring high optical purity.
    Physical Properties

    Melting Point: 181-186 °C

    mg g kg ml l t