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his pioneering work on paracyclophane chemistry, Cram identified 3 as a byproduct in his attempts to reduce the corresponding diazonium salt with hypophosphoric acid
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Results from our laboratories
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0002737051
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Only indirect resolution methods using enzymes are known. In all cases, 4-acetoxy[2.2]paracyclophane is used as a substrate hydrolyzed via kinetic resolution to enantioenriched 3
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The use of the Dakin reaction in the paracyclophanes series
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The use of the Dakin reaction in the paracyclophanes series: Rozenberg, V. I.; Antonov, D. Y.; Sergeeva, E. V.; Vorontsov, E. V.; Starikova, Z. A.; Fedyanin, I. V.; Schulz, C.; Hopf, H. Eur. J. Org. Chem. 2003, 2056-2061
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It was also shown that a resolution of the corresponding aldehyde (6) with enantiopure 1-phenyl-2-(4-methylphenyl)ethylamine proceeds in 29% yield over two steps
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It was also shown that a resolution of the corresponding aldehyde (6) with enantiopure 1-phenyl-2-(4-methylphenyl)ethylamine proceeds in 29% yield over two steps: Banfi, S.; Manfredi, A.; Montanari, F.; Pozzi, G.; Quici, S. J. Mol. Catal. A: Chem. 1996, 113, 77-86
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The absolute configuration of the diastereomers of 8 was verified by comparison with literature values (see ref 21)
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The absolute configuration of the diastereomers of 8 was verified by comparison with literature values (see ref 21).
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