A new precursor of a formal 1-hydroxy allyl anion is represented by 3-bromo-1-acetoxy-1-propene, which is synthesized by the ZnCl2-catalyzed addition of acetyl bromide to propenal. 3-Bromo-1-acetoxy-1-propene reacts with indium powder in THF to give the corresponding 3-acetoxylated ally indium complex, which regioselectively adds to aldehydes, affording monoprotected 1-en-3,4-diols. Diastereoselectivity mainly depends on the nature of the aldehyde; saturated aldehydes afford anti adducts, whereas the r,â-unsaturated aldehydes preferentially lead to the syn isomers

A new protocol for the acetoxyallylation of aldehydes mediated by indium in THF

Lombardo M.
;
Morganti S.;Trombini C.
2001

Abstract

A new precursor of a formal 1-hydroxy allyl anion is represented by 3-bromo-1-acetoxy-1-propene, which is synthesized by the ZnCl2-catalyzed addition of acetyl bromide to propenal. 3-Bromo-1-acetoxy-1-propene reacts with indium powder in THF to give the corresponding 3-acetoxylated ally indium complex, which regioselectively adds to aldehydes, affording monoprotected 1-en-3,4-diols. Diastereoselectivity mainly depends on the nature of the aldehyde; saturated aldehydes afford anti adducts, whereas the r,â-unsaturated aldehydes preferentially lead to the syn isomers
2001
Lombardo M.; Girotti R.; Morganti S.; Trombini C.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/897740
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