(1R,2S)-(+)-10,2-Camphorsultam

• Catalog No.: A14133
• CAS Number: 108448-77-7
• M. F.: C10H17NO2S
• M. W.: 215.31248
• Purity: 99%

SYNONYMS

• Title: (1R,2S)-(+)-2,10-樟脑磺内酰胺
• IUPAC name: (1R,5R,7R)-10,10-dimethyl-3λ^6-thia-4-azatricyclo[5.2.1.0^1,^5]decane-3,3-dione
• IUPAC Traditional name: (1R,5R,7R)-10,10-dimethyl-3λ^6-thia-4-azatricyclo[5.2.1.0^1,^5]decane-3,3-dione
• Synonyms: (2S)-(+)-Bornane-10,2-sultam

DATABASE IDS

• CAS Number: 108448-77-7
• Beilstein Number: 4675755
• MDL Number: MFCD00151762

PROPERTIES

• Purity: 99%
• Melting Point: 179-186°C
• Optical Rotation: +33 (c=1 in ethanol)
• GHS Hazard statements: H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 否

REFERENCES

• Versatile chiral auxiliary introduced by Oppolzer. Review: Tetrahedron, 49, 293 (1993). The N-acyl derivatives undergo various transformations in a highly enantioselective manner:
• N-Acryloyl derivatives undergo enantioselective cycloaddition reactions: Helv. Chim. Acta, 67, 1397 (1984); Tetrahedron, 43, 1969 (1987). Hydrogenation of N-acryloyl derivatives proceeds with high diastereoselectivity: Tetrahedron Lett., 27, 183 (1986); Helv. Chim. Acta, 69, 1542 (1986), 69, 1817 (1986); 70, 1666 (1987). Induces asymmetric conjugate addition of Grignard reagents to N-acryloyl derivatives: Helv. Chim. Acta, 70, 2201 (1987). In the presence of strong bases, N-acyl derivatives undergo stereoselective alkylation: Tetrahedron Lett., 30, 5603 (1989); or aldol-type condensation reactions with aldehydes: J. Am. Chem. Soc., 112, 2767 (1990); Tetrahedron Lett., 32, 61 (1991).
• Chiral auxiliary for the asymmetric Baylis-Hillman reaction (see 1,4-Diazabicyclo[2.2.2]octane, A14003): J. Am. Chem. Soc., 119, 4317 (1997).