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Thiophosphoramide 5d was found to be an effective organocatalyst for the enantioselective Michael reaction of problematic acetone to various hydroxymethyl nitrostyrenes, affording the multisubstituted tetrahydropyrans with three stereogenic centers. The Michael addition products generated were obtained as a single diastereomer with enantioselectivities ranging from 46% to 74% ee.
In the presence of an effective air-stable nucleophilic trialkylphosphine organocatalyst, 1,3,5-triaza-7-phosphaadamantane, a chiral N-thiophosphoryl imine bearing a (S)-binaphthalene skeleton induced a diastereoselective aza-MBH reaction with fair chemical yields and moderate to excellent diastereoselectivities (up to >99% de).
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