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The "naked" alkoxide 1 of (S)-6-methyl-δ-lactol acts as an excellent chiral hydroxide equivalent in highly diastereoselective oxy-Michael additions to nitroalkenes (see scheme). The excellent stereoinduction arises from what becomes a superb protecting group in the resulting 1,2-amino alcohol products. R1 = alkyl, aryl, furanyl, thiophenyl; R2,R 3 = -(CH2)3CHCH3O-.
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Adderley et al. (2003) studied this question.
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