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Origin of the Diastereoselection in the Indium-Mediated Addition of Haloallylic Sulfones to Aldehydes

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NIAID Data Ecosystem2026-03-06 收录
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The R1 substituents at C(2) of the haloallylic sulfones 1 play a pivotal role in controlling the diastereoselectivity of the indium-mediated addition reaction to benzaldehyde to produce the homoallylic alcohols 3. The R1 Me group of 1 prefers the chair form in the In-coordinated six-membered cyclic transition state to give anti-3a, and the R1 Ph group of 1 favors the twist boat form to give syn-3n, both in a high 13:1 selectivity.

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2006-03-30
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