Tetrahedron

Oxazaborolidine-catalysed reduction of alk-2-ene-1, 4-diones. A convenient access to chiral 1, 4-diols

J Bach, R Berenguer, J Garcia, M López, J Manzanal…

Index: Bach, Jordi; Berenguer, Ramon; Garcia, Jordi; Lopez, Marta; Manzanal, Judith; Vilarrasa, Jaume Tetrahedron, 1998 , vol. 54, # 49 p. 14947 - 14962

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Citation Number: 41

Abstract

An efficient method for the preparation of C2-symmetric, chiral alk-2-ene-1, 4-diols (4) has been achieved, based on the borane-mediated reduction of symmetric alk-2-ene-1, 4-diones (2) in the presence of oxazaborolidine (R)-1. In general, the presence of the double bond in 2 has been beneficial (compared with the related saturated 1, 4-diketones 3) not only as far as the stereoselectivity in the reduction step is concerned, but also because it allowed us ...