Origin of the diastereoselection in the indium-mediated addition of haloallylic sulfones to aldehydes.
Org Lett
; 8(7): 1459-62, 2006 Mar 30.
Article
em En
| MEDLINE
| ID: mdl-16562916
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 131 selectivity.
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2006
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Article