Leaving groups nucleophilic substitution, asymmetric allylation

The Tsuji-Trost reaction is the palladinum-catalyzed substitution of allylic leaving groups by carbon nucleophiles. The nucleophile can be carbon-, nitrogen-, or oxygen- based compounds such as alcohols, enolates, phenols, and enamines, and the leaving group can be a halide or an acetate. This emerged as a powerful procedure for the formation of C—C, C—O and C—N bonds. The reaction, also known as Trost allylation or allylic alkylation, was named after Jiro Tsuij, who first reported the method in 1965 [42], and Barry Trost, who introduced an asymmetric version in 1973 [43]. 

The rearrangement of a-sulfonimidoyl-/3,y-unsaturated esters paved the way for a promising synthesis of y-amino acids in fair yields (Scheme 24). In the presence of a chiral ligand, such as BINAP, moderate asymmetric induction has been reported (20-60% ee). The demonstrated leaving capability of the sufoximino group has been utilized in allylic substitution with typical nucleophiles, such as sodium diethyl malonate, dibenzy-lamine, and t-butyl N-(diphenyhnethylene)glycinate. ... 

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