Isobutylmagnesium bromide

The sulfoxide substituent was also used to introduce the C(10)-C(13) fragment and was reduced to a vinyl sulfide in Step B-l. In Step C-l, the vinyl sulfide was hydrolyzed to an aldehyde, which was elaborated by addition of isobutylmagnesium bromide. 

Esters can be reduced under these conditions to cither secondary or primary alcohols, depending on the amount of CpjTiCK used. In the presence of 2 mole % of catalyst, isobutylmagnesium bromide reduces esters mainly to the corresponding primary alcohols. When less catalyst is used, the major products arc secondary alcohols formed by coupling of the ester and the Grignard reagent.3... 

COOH-> —CHO Reaction of a carboxylic acid with isobutylmagnesium bromide and catalytic amounts of titanocene dichloride affords aldehydes in fair to moderate yield (equation I). The reaction fails with a,/ -unsaturated acids. 

Hydromagnesiation butenolides.1 Reaction of optically pure y-trimethylsilyl propargylic alcohols with isobutylmagnesium bromide catalyzed by Cp2TiCl2 (14,... 

HydromagnesiatUm vinylsilanes. The hydromagnesiation (10, 130-131) of 1-trimethylsilyl-1 -alkynes with isobutylmagnesium bromide followed by alkylation affords (Z)-l,2-dialkylvinylsilanes in high yield. 

Now, how do we make 3-nrpthyl-l-butanol It is a primary alcohol and contains one carbon more than our largest available alcohol therefore we would use the reaction of a Grignard reagent with formaldehyde. The necessary Grig-nard reagent is isobutylmagnesium bromide, which we could have prepared from... 

Rose oxide (240) (32% cis, 68% trans) and dihydrorose oxide were synthesized efficiently by the action of isobutenylmagnesium bromide or isobutylmagnesium bromide on the ether (24Synthesis of dehydrorose oxide, rose oxide (240), and... 

H. Ishikawa, S. Ikeda, and T. Mukaiyama, Chem. Letters, 1975, 1051 a reaction scheme confusingly implies that rose oxide reacts with isobutylmagnesium bromide to yield dihydrorose oxide, and Current Abstracts of Chemistry and Index Chemicus, Abstract No. 238 491, perpetuates this ... 

Carbohydrates are important chiral, non-racemic precursors (chiral templates) to statine and its derivatives. Aldehyde 6.138 0 as converted to alcohol 6.139 by reaction with isobutylmagnesium bromide. After conversion to a benzoate (6.140), displacement with sodium azide gave 6.141. The tetrahydrofuran ring was opened and oxidation gave 6.142. Oxidation of the aldehyde and then reduction of the azide moiety led to (+)-statine (3R,4S-tf.P5). Reaction of 6.139 with mesyl chloride and then sodium benzoate gave the benzoate (6.140) of opposite absolute configuration, which was converted to (-)-statine (3S,4R-t. 95) by the same sequence. 

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