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2005
Amino acids
U 0400
Stereospecific, Enantioselective Allylation of α-Hydrazono Esters by Using Allyltrichlorosilanes with BINAP Dioxides as Neutral-Coordinate Organocatalysts.
14- 191 —
BINAP dioxides are used as chiral neutral-coordinate organocatalysts for the enantioselective allylation of α-hydrazono esters using allyltrichlorosilanes. Allylated adducts are obtained with high diastereo- and enantioselectivities. (E)-allylic silanes give
syn-adducts, while anti-adducts are obtained from (Z)-allylic silanes. The present reaction as the first example of a stereospecific, enantioselective allylation of α-imino esters is applied to an efficient synthesis of D-alloisoleucine (VI) by further reduction of
(V). — (OGAWA, C.; SUGIURA, M.; KOBAYASHI*, S.; Angew. Chem., Int. Ed. 43
(2004) 47, 6491-6493; Grad. Sch. Pharm. Sci., Univ. Tokyo, Bunkyo, Tokyo 113,
Japan; Eng.) — S. Adam
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