The asymmetric oxa-Michael addition of (-)-N-formylnorephedrine, a chiral oxygen nucleophile with a removable auxiliary, to (E)-nitroalkenes 1 permits the enantioselective synthesis of protected vicinal amino alcohols (R)-3 with high enantiomeric excesses after reduction of the 1,4-adducts 2. This new procedure opens an efficient entry to synthetic building blocks for natural products and drugs.
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Enders et al. (1996) studied this question.
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