Origin of the diastereoselection in the indium-mediated addition of haloallylic sulfones to aldehydes.
[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.
Min
Jae-Hong
JH
Department of Chemistry, Myong Ji University, Yongin, Kyunggi-Do, 449-728, Korea.
Jung
Se-Young
SY
Wu
Bo
B
Oh
Jung Taek
JT
Lah
Myoung Soo
MS
Koo
Sangho
S