1975
DOI: 10.1055/s-1975-23856
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Applications of Diisobutylaluminium Hydride (DIBAH) and Triisobutylaluminium (TIBA) as Reducing Agents in Organic Synthesis

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Cited by 263 publications
(66 citation statements)
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“…An attempt to derivatize the secondary hydroxy group of 2 as its Mosher esters failed. However, formation of Mosher esters and the assignment of the absolute configuration of 2 was possible after reduction of the keto group with DIBAL-H. [17] The reduction yielded two epimeric alcohols 18 (pseudoequatorial hydroxy group) and 19 (pseudoaxial hydroxy group) (see Supporting Information), which gave smooth access to the corresponding Mosher ester pairs (R/ the two epimers showed a disturbed distribution of positive and negative shift differences due to steric congestion in the vicinity. However, chemical shift analysis of the pseudoaxial esters (R/S)-21a and (R/S)-21b demonstrated an even distribution of chemical shift differences and allowed the configurations of the stereogenic centers at C-4 in (R/S)-21a and (R/S)-21b to be assigned as (R).…”
Section: Resultsmentioning
confidence: 99%
“…An attempt to derivatize the secondary hydroxy group of 2 as its Mosher esters failed. However, formation of Mosher esters and the assignment of the absolute configuration of 2 was possible after reduction of the keto group with DIBAL-H. [17] The reduction yielded two epimeric alcohols 18 (pseudoequatorial hydroxy group) and 19 (pseudoaxial hydroxy group) (see Supporting Information), which gave smooth access to the corresponding Mosher ester pairs (R/ the two epimers showed a disturbed distribution of positive and negative shift differences due to steric congestion in the vicinity. However, chemical shift analysis of the pseudoaxial esters (R/S)-21a and (R/S)-21b demonstrated an even distribution of chemical shift differences and allowed the configurations of the stereogenic centers at C-4 in (R/S)-21a and (R/S)-21b to be assigned as (R).…”
Section: Resultsmentioning
confidence: 99%
“…The mass ratio of the two polymers b It was not possible to detect either the aldehyde or the alcohol as end groups by 1 H NMR, but most probably alcohol end groups are formed since the reduction to aldehydes is described as a ''low temperature reduction''. [17] In contrast our experimental temperature was T ¼ 60 8C.…”
Section: Preparation Of the Compatibilized Br/pcl Blendmentioning
confidence: 73%
“…In brief, among the tested conditions, the best one was the reaction carried out in methylene chloride at 08C; it resulted in the intermediate 5 [35]. Many compounds and nearly all important functional groups have been tested as adducts for highly reactive alkylaluminium hydrides [36]. Their popularity has risen considerably due to several reasons, such as, diisobutylaluminium hydride has proved to be safe and easy-tohandle in toluene or hexane.…”
Section: Resultsmentioning
confidence: 99%