Titanium chloride-Diisobutylaluminum hydride

Titanium(III) chloride-Diisobutylaluminum hydride. A black, solid lower-valent titanium reagent (1) is obtained on reduction of TiCl3 3THF with DIBAH in toluene.1... 

Oxidation reactions r-Butyl hydroperoxide-Dialkyl tar-trate-Titanium(IV) isopropoxide, 51 m-Chloroperbenzoic acid, 76 Reduction reactions Chlorodiisopinocampheylborane, 72 Diisobutylaluminum hydride-Tin(II) chloride- (S) -1 - [ l-Methyl-2-pyrrolidi-nyljmethylpiperidine, 116 Lithium borohydride, 92 Lithium tri-sec-butylborohydride, 21 B-3-Pinanyl-9-borabicyclo[3.3.1]-nonane, 249... 

Dialkylpyrrolines are reduced by diisobutylaluminum hydride stereospecifically to give m-tetrahydropyrroles with or without Lewis acid12. Lithium aluminum hydride alone, or in the presence of titanium(IV) chloride or trimethyl aluminum, also reduces 2,5-dialkylpyrrolines to rL-tetrahydropyrroles. On the other hand, sodium borohydride gives an equal mixture of cis-and ran.v-tetrahydropyrroles, but in the presence of nickel(II) chloride or titanium(IV) chloride the major component obtained is always the cu-diastereomer12. 

FURANES Diisobutylaluminum hydride. Phenylselenenyl chloride. Titanium tetrachloride. 

Triethylsilane in 3M ethereal Lithium Perchlorate solution effects the reduction of secondary allylic alcohols and acetates (eq 18). The combination of triethylsilane and Titanium(IV) Chloride is a particularly effective reagent pair for the selective reduction of acetals. Treatment of ( )-frontalin with this pair gives an 82% yield of tetrahydropyran products with a cis. trans ratio of 99 1 (eq 19). This exactly complements the 1 99 product ratio of the same products obtained with Diisobutylaluminum Hydride. ... 

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