Enantioselective chemoenzymatic synthesis of cis-and trans-2, 5-disubstituted morpholines

…, S Hoekman, ED Verdasco, FL van Delft…

Index: Ritzen, Bas; Hoekman, Steven; Verdasco, Elena Duran; Van Delft, Floris L.; Rutjes, Floris P. J. T. Journal of Organic Chemistry, 2010 , vol. 75, # 10 p. 3461 - 3464

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Citation Number: 25

Abstract

A versatile synthesis of enantiomerically pure cis-and trans-2, 5-disubstituted morpholines is described. Hydroxynitrile lyase-mediated cyanide addition onto aldehydes provided cyanohydrins in virtually quantitative yield and excellent enantioselectivity. Subsequent formation of diastereomerically pure amino esters via a three-step, one-pot reduction− transimination− reduction sequence followed by reduction and simultaneous protection ...