Asymmetric Induction of the Iodolactonization Reaction of α-Sulfurated γ-Unsaturated Amides
- 22 January 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (4) , 1196-1201
- https://doi.org/10.1021/jo035488b
Abstract
The 1,3-asymmetric iodolactonization reaction of enantiopure alpha-sulfurated gamma-unsaturated amides has been investigated. With sulfinyl and sulfonyl groups, a poorly stereoselective reaction was observed, whereas with a sulfanyl moiety, the diastereoselectivity can be high as 96:4. The role of the oxygen atom on the sulfur moiety is discussed.Keywords
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