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
Lombardo M., Girotti R., Morganti S., Trombini C. (2001). A new protocol for the acetoxyallylation of aldehydes mediated by indium in THF. ORGANIC LETTERS, 3(19), 2981-2983 [10.1021/ol016315g].
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 isomersI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
