Concise, stereodivergent and highly stereoselective synthesis of cis-and trans-2-substituted 3-hydroxypiperidines–development of a phosphite-driven …

…, JC Westphal, AMP Koskinen

Index: Huy, Peter H.; Westphal, Julia C.; Koskinen, Ari M.P. Beilstein Journal of Organic Chemistry, 2014 , vol. 10, p. 369 - 383

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Citation Number: 7

Abstract

Abstract A concise (5 to 6 steps), stereodivergent, highly diastereoselective (dr up to> 19: 1 for both stereoisomers) and scalable synthesis (up to 14 g) of cis-and trans-2-substituted 3- piperidinols, a core motif in numerous bioactive compounds, is presented. This sequence allowed an efficient synthesis of the NK-1 inhibitor L-733,060 in 8 steps. Additionally, a cyclodehydration-realizing simple triethylphosphite as a substitute for triphenylphosphine ...