Biomimetic reductions of benzaldehyde and acetophenone by models of NAD(P)H

✍ Scribed by Yutaka Ohnishi; Miyoko Kitami

• Publisher: Elsevier Science
• Year: 1978
• Tongue: French
• Weight: 158 KB
• Volume: 19
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)95131-7

✦ Synopsis

With respect to enzymatic reductions of carbonyl compounds by reduced pyridine nucleotides,NAD(P)H,wedescribedpreviouslychemicalreduction, assisted by a divalent metal ion such as Mg++ or Zn ++,of a-keto esters with 1-benzyl-1,4dihydronicotinamide(BNAH) as a model of NAD(P)H'! This mimicry has beenextended 3) to the reduction of a-diketones, a-hydroxy ketones , and 2-acylpyridines 4) . Magnesium ion also promoted largely the reduction of a,a,a-trifluoroacetophenone in non-aqueous media 5) , but the reduction of benzaldehyde has not yet been effected under similar conditions because of low reactivity of BNAH forit.

Recently, Shirra and Suckling described that benzaldehydes afforded the benzyl