Synlett

Preparation of (Z)-1-Halo-1-alkenes and (Z)-1-Halo-2-alkoxy-1-alkenes Using Cr (II/III) and Fe (0)

JR Falck, A He, R Bejot, C Mioskowski

Index: Falck; He, Anyu; Bejot, Romain; Mioskowski, Charles Synlett, 2006 , # 16 p. 2652 - 2654

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Citation Number: 4

Abstract

A survey of inexpensive, eco-friendly reductants revealed Fe(0) and Mn(0) [4] were the most promising and these were thus singled out for optimization using the conversion of trichloride 1 to (Z)-1-chloro-1-alkene 2 as the test system (Table [1] ). Utilizing one equivalents of CrCl 2 and three equivalents of either Fe(0) or Mn(0) in anhydrous tetrahydrofuran at ambient temperature, 2 was generated with complete Z stereoselectivity (>99%) as judged by 1 H/ ...