Tetrahedron Letters p. 139 - 142 (1987)
Update date:2022-07-30
Topics:
Keck, Gary E.
Abbott, Duain E.
Wiley, Michael R.
The preparation of allylstannanes 1a-c, all of which bear an oxygen substituent at the allylic terminus, is desribed.These reagents react with alpha- and beta-alkoxyaldehydes in the presence of MgBr2 as Lewis acid to give SE' products with diastereofacial selectivity consistent with "chelation control"; a syn disposition of substituents about the newly formed bond is highly favored in all cases.
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