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The bisprotected amino ketone 3 is expected to give syn amino alcohol by assuming external hydride delivery to the less hindred face of the carbonyl of 3 existing in a non chelated conformation (Felkin-Ahn model). In contrast, the keto sulfoxide 3 is expected to give the anti amino alcohol, assuming hydride delivery from the same side as the sulfinyl oxygen previously chelated to DIBAL.
-
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27
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0009646871
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note
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5S: C, 59.50; H, 7.61; N, 3.65; S, 8.36. Found: C, 59.57; H, 7.85; N, 3.68; S, 8.15.
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