Abstract
E)-3-Bromo-1-phenylsulfonylprop-1-ene and (E)-3-iodo-1-phenylsulfonylprop-1-ene both form allylic organozinc reagents that react with aromatic aldehydes to give mainly 4-aryl-4-hydroxy1-phenylsulfonylbut-1-enes. In contrast, reactions of the same organozinc species with 2-methylpropanal or 3-methylbutanal gave mixtures of diastereoisomeric 4-hydroxy-1-phenylsulfonylalk1-enes and 4-hydroxy-3-phenylsulfonylalk-1-enes.
Highlights
We have previously reported[1] that the (E)-3-halo-1-phenylsulfonylpropenes 1-3 and the (Z)-1halo-3-phenylsulfonylpropenes 4 and 5 can be lithiated to give hetero-substituted carbanions
We demonstrate that useful organozinc reagents can be prepared from the halosulfones 2 and 3, and that these react with aldehydes to yield Reformatsky-like products
The organozinc reagent derived from the bromosulfone 2 reacted (Scheme 1) with 4-chlorobenzaldehyde to give a mixture of the (E)- and (Z)-γ-alkylated products 13 and 14 in 93:7 ratio, with 3-fluorobenzaldehyde to give a mixture of (E)-15, (Z)-16 and anti-17, and with 3-methoxybenzaldehyde to give (E)-18 and (Z)-19
Summary
We have previously reported[1] that the (E)-3-halo-1-phenylsulfonylpropenes 1-3 and the (Z)-1halo-3-phenylsulfonylpropenes 4 and 5 can be lithiated to give hetero-substituted carbanions. The organozinc reagent derived from the bromosulfone 2 reacted (Scheme 1) with 4-chlorobenzaldehyde to give a mixture of the (E)- and (Z)-γ-alkylated products 13 and 14 in 93:7 ratio, with 3-fluorobenzaldehyde to give (by NMR) a mixture of (E)-15, (Z)-16 (minor) and anti-17, and with 3-methoxybenzaldehyde to give (E)-18 and (Z)-19.
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