Enantio-and diastereoselective synthesis of all four possible stereoisomers of 2-(phenylhydroxymethyl) quinuclidine

B Lygo, J Crosby, TR Lowdon, PG Wainwright

Index: Lygo, Barry; Crosby, John; Lowdon, Terence R.; Wainwright, Philip G. Tetrahedron Letters, 1997 , vol. 38, # 13 p. 2343 - 2346

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Citation Number: 28

Abstract

An enantio-and diastereoselective synthesis of all four possible stereoisomers of 2- (phenylhydroxymethyl) quinuclidine is reported. Key steps involve the use of the Sharpless dihydroxylation protocol to induce asymmetry, and stereodivergent cyclisations of the resulting diol to form the quinuclidine ring.