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Lipase catalysed resolution of ferrocene cyanohydrin: access to novel ferrocenyl aminoalcohols and diamines

✍ Scribed by James A.S. Howell; Kristina Humphries; Patrick McArdle; Desmond Cunningham; Giovanni Nicolosi; Angela Patti; Martin A. Walsh


Book ID
104361119
Publisher
Elsevier Science
Year
1997
Tongue
English
Weight
199 KB
Volume
8
Category
Article
ISSN
0957-4166

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✦ Synopsis


R)-(+)-Ferrocene cyanohydrin acetate, obtained by enzymatic acylation of ferrocene cyanohydrin, may be transformed by reduction and alkylation into novel ferrocenyl I~-aminoalcohols. Substitution of acetate by methanolic HNMe2 proceeds with racemisation, but significant diastereoselection is observed on Strecker reaction using (-)-PhCH(Me)NHMe. (~ 1997 Elsevier Science Ltd


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A series of novel (R)-5-phenylfuran-2-yl cyanomethyl butanoates were prepared by Pseudomonas cepacia lipasecatalysed dynamic kinetic resolution in toluene. The method exploits a basic resin both for the racemization and formation of phenylfuran-based cyanohydrins and for the decomposition of acetone