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Ferrocenylamines possessing planar chirality have been extensively used to catalyze asymmetric reactions of ketoketenes, see
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Reference 9a
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Reference 9a.
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84904448377
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MOP, BINAP, and various phosphepines gave low enantioselectivity (<30% ee) for the dimerization of methylphenylketene 1a
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MOP, BINAP, and various phosphepines gave low enantioselectivity (<30% ee) for the dimerization of methylphenylketene 1a.
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39
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84904448369
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Josiphos derivatives 4a - e are available from Aldrich and from Strem
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Josiphos derivatives 4a - e are available from Aldrich and from Strem.
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40
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84904448370
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Josiphos-catalyzed homodimerization of isopropylmethylketene also gave the 1,3-cyclobutanedione regioisomer, with only trace β-lactone being formed
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Josiphos-catalyzed homodimerization of isopropylmethylketene also gave the 1,3-cyclobutanedione regioisomer, with only trace β-lactone being formed.
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The relative stereochemistry of 10b was confirmed to be syn by a comparison with the spectroscopic data presented in ref 8. The relative stereochemistry of 8a has not been determined. Both 8a and 9a were determined to be optically active (see the Supporting Information) but the ee values of 8a and 9a were not determined unambiguously by HPLC analysis. However, as no bonds at the quaternary stereocenter are cleaved in the formation of 8a or 9a, retention of chirality is assumed
-
The relative stereochemistry of 10b was confirmed to be syn by a comparison with the spectroscopic data presented in ref 8. The relative stereochemistry of 8a has not been determined. Both 8a and 9a were determined to be optically active (see the Supporting Information) but the ee values of 8a and 9a were not determined unambiguously by HPLC analysis. However, as no bonds at the quaternary stereocenter are cleaved in the formation of 8a or 9a, retention of chirality is assumed.
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