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Versatile chiral auxiliary introduced by Oppolzer. Review: Tetrahedron, 49, 293 (1993). The N-acyl derivatives undergo various transformations in a highly enantioselective manner:/n
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)./n
Chiral auxiliary for the asymmetric Baylis-Hillman reaction (see 1,4-Diazabicyclo[2.2.2]octane, A14003): J. Am. Chem. Soc., 119, 4317 (1997)./n
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant