Origin of the diastereoselection in the indium-mediated addition of haloallylic sulfones to aldehydes |
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Authors: | Min Jae-Hong Jung Se-Young Wu Bo Oh Jung Taek Lah Myoung Soo Koo Sangho |
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Institution: | Department of Chemistry, Myong Ji University, Yongin, Kyunggi-Do, 449-728, Korea. |
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Abstract: | reaction: see text] The R(1) 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 R(1) Me group of 1 prefers the chair form in the In-coordinated six-membered cyclic transition state to give anti-3a, and the R(1) Ph group of 1 favors the twist boat form to give syn-3n, both in a high 13:1 selectivity. |
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