Journal
ORGANIC LETTERS
Volume 4, Issue 21, Pages 3619-3622Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol026563s
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[GRAPHICS] Efficient 1,4-asymmetric induction with an enantiopure aminoalkyl group as the chiral auxiliary has been achieved in the first example of diastereoselective alkylation (up to 98:2) of a sulfenate anion, readily prepared by oxidation of the corresponding thiolate. The stereochemistry of the sulfoxide produced is the opposite of that obtained by the conventional route based on oxidation of the sulfide precursor.
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