Tetrahedron

Enantioenriched ω-bromocyanohydrin derivatives. Improved selectivity by combination of two chiral catalysts

R Hertzberg, K Widyan, B Heid, C Moberg

Index: Hertzberg, Robin; Widyan, Khalid; Heid, Berenice; Moberg, Christina Tetrahedron, 2012 , vol. 68, # 37 p. 7680 - 7684

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Citation Number: 4

Abstract

Highly enantioenriched (R)-4-bromo-1-cyanobutyl acetate and (R)-5-bromo-1-cyanopentyl acetate were prepared by acetylcyanation of 4-bromobutanal and 5-bromopentanal, respectively, catalyzed by (S, S)-[(4, 6-bis (t-butyl) salen) Ti (μ-O)] 2 and triethylamine followed by enzymatic hydrolysis of the minor enantiomer. A cyclic procedure employing the same two chiral catalysts provided inferior results due to a slowly reached steady state ...