Preparation of 2-trimethylsilylmethyl-1-alkene; cross-coupling and protodesilylation sequence from 1,1-dibromo-1-alkene
摘要:
A new method for the preparation of exomethylene type allylsilane is described. Selective mono-protodesilylation of 1-trimethylsityl-2-trimethylsilylmethyl-2-alkenes 2 with PPTS afforded 2-trimethylsilylmethyl-l-alkeiles 4 in excellent yields. Since the resulting allylsilanes 4 possess an exomethylene unit, the reactions of 4 with carbonyl compounds in the presence of Lewis acids gave the corresponding product 7 having an exomethylene unit in excellent yields. (c) 2007 Elsevier Ltd. All rights reserved.
Preparation of 2-trimethylsilylmethyl-1-alkene; cross-coupling and protodesilylation sequence from 1,1-dibromo-1-alkene
摘要:
A new method for the preparation of exomethylene type allylsilane is described. Selective mono-protodesilylation of 1-trimethylsityl-2-trimethylsilylmethyl-2-alkenes 2 with PPTS afforded 2-trimethylsilylmethyl-l-alkeiles 4 in excellent yields. Since the resulting allylsilanes 4 possess an exomethylene unit, the reactions of 4 with carbonyl compounds in the presence of Lewis acids gave the corresponding product 7 having an exomethylene unit in excellent yields. (c) 2007 Elsevier Ltd. All rights reserved.
Electrophilic reactions of 3-phenyl-1,1-bis(trimethylsilymethyl)-1-propene (1) and 1,1-bis[dimethyl(phenyl)silylmethyl]-3-phenyl-1-propene (4) are described. Protodesilylation of 1 with PPTS gave 2-substituted allylsilane (2) in excellent yield. Halogenation of 4 with N-halosuccimide gave a mixture of 3-halo-5-phenyl-2-silylmethyl-l-pentene (5) and 3-halo-5-phenyl-1,2bis(silylmethyl)-1-pentene (6). The reaction of 1 and 4 with ozone gave no carbonyl compounds but gave 3-hydoxy-5-phenyl-2-silylmethyl-1-pentene (7).