Palladium (0)-catalyzed azidation of allyl esters. Selective synthesis of allyl azides, primary allylamines, and related compounds

S Murahashi, Y Taniguchi, Y Imada…

Index: Murahashi, Shun-Ichi; Taniguchi, Yuki; Imada, Yasushi; Tanigawa, Yoshio Journal of Organic Chemistry, 1989 , vol. 54, # 14 p. 3292 - 3303

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Citation Number: 199

Abstract

Palladium (0)-catalyzed reaction of allyl esters such as phosphates, carbonates, and carboxylates with sodium azide gives allyl azides. The azidation proceeds with retention of configuration at the allylic carbon. Optically active (R)-(E)-(+)-4-phenyl-3-buten-2-~ 1 azide (19) is obtained from (R)-(E)-(+)-4-phenyl-3-buten-2-~ 1 acetate (18) stereoselectively. Sequential substitution of (Z)-4-acetoxy-2-buten-l-y1 diethyl phosphate (24) with ...