Copper Chloride-Catalyzed and Hydrochloric Acid-Mediated Chemoselective Protiodestannylations of Alkyl (Z)- or (E)-2,3-Bis(trimethylstannyl)-2-alkenoates. Stereoselective Preparation of Alkyl (E)- and (Z)-3-Trimethylstannyl-2-alkenoates
摘要:
Treatment of alkyl (Z)-2,3-bis(trimethylstannyl)-2-alkenoates (7) with a catalytic amount of copper(I) chloride in N,N-dimethylformamide (DMF) containing a small quantity of water provides very good-to-excellent yields of alkyl (E)-3-trimethylstannyl-2-alkenoates (1). On the other hand, stirring of solutions of alkyl (Z)-(7) or (E)-2,3-bis(trimethyIstannyl)-2-alkenoates (8) in DMF containing dilute hydrochloric acid produces, efficiently, alkyl (Z)-3-trimethylstannyl-2-alkenoates (2).
Copper Chloride-Catalyzed and Hydrochloric Acid-Mediated Chemoselective Protiodestannylations of Alkyl (<i>Z</i>)- or (<i>E</i>)-2,3-Bis(trimethylstannyl)-2-alkenoates. Stereoselective Preparation of Alkyl (<i>E</i>)- and (<i>Z</i>)-3-Trimethylstannyl-2-alkenoates
作者:Edward Piers、Ernest J. McEachern、Miguel A. Romero
DOI:10.1021/jo9707693
日期:1997.8.1
Treatment of alkyl (Z)-2,3-bis(trimethylstannyl)-2-alkenoates (7) with a catalytic amount of copper(I) chloride in N,N-dimethylformamide (DMF) containing a small quantity of water provides very good-to-excellent yields of alkyl (E)-3-trimethylstannyl-2-alkenoates (1). On the other hand, stirring of solutions of alkyl (Z)-(7) or (E)-2,3-bis(trimethyIstannyl)-2-alkenoates (8) in DMF containing dilute hydrochloric acid produces, efficiently, alkyl (Z)-3-trimethylstannyl-2-alkenoates (2).
Peesapati, Venkateswarlu; Nagarapu, Lingaiah, Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1993, vol. 32, # 7, p. 790 - 792