Tetrahedron

Geminal dialkylation, alkylative reduction and olefination of aliphatic aldehydes. Reaction of gem-bistriflates with higher order dialkylcyanocuprates.

AG Martínez, JO Barcina, BR Díez, LR Subramanian

Index: Garcia Martinez; Osio Barcina; Ruiz Diez; Subramanian Tetrahedron, 1994 , vol. 50, # 46 p. 13231 - 13238

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Abstract

gem-Dialkylation or alkylative reduction of α-unbranched aliphatic aldehydes 1 is advantageously achieved by reaction of the corresponding gem-bistriflates 2 with di-n- alkylcyanocuprates or di-sec-and di-tert-alkylcyanocuprates respectively. The reaction of α- branched gem-bistriflates 2 with dialkylcyanocuprates in the presence of boron trifluoride affords the olefins 6 in good yield.

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