Journal of Organic Chemistry p. 638 - 642 (1991)
Update date:2022-07-29
Topics:
Barrett, Anthony G. M.
Flygare, John A.
α-Iodo silanes 8 were prepared from α-hydroxy silanes and after halogen/metal exchange and treatment with copper(I)bromide-dimethyl sulfide were coupled with acid chlorides to yield α-silyl ketones 2.Cram controlled addition with a variety of nucleophiles followed by treatment with acid or base led to either the (E)- or (Z)-alkene in good overall yields from the iodide (47-67percent) and with excellent stereoselectivities (>95/<5 for disubstituted cases and 67/33 to 95/5 for trisubstituted).The procedure was used iteratively in the total synthesis of 4(E)8(Z)-tetradecadien-1-yl acetate (15) in >95/<5 isomeric purity.
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