Comparative study of the diastereoselective addition of allenyl zinc reagents to alpha-alkoxy (or silyloxy) aldehydes and imines. A straightforward synthesis of amino alcohols from imines
The addition of allenylzinc bromides to alpha-chiral imines proceeds with very high diastereoselectivity. This result is in contrast with the addition to the corresponding aldehydes, leading to poor diastereoselectivity. The anti/anti adducts are explained by Felkin-Ahn and Gaudemar-Yamamoto models of the transition state.
Poisson
JF
Laboratoire de Chimie des Organoelements, Universite Pierre et Marie Curie, Paris, France.
Normant
JF