Wm. Clark et al., A highly enantioselective conjugate reduction of 3-arylinden-1-ones using bakers' yeast for the preparation of (S)-3-arylindan-1-ones, ORG LETT, 1(11), 1999, pp. 1839-1842
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The bakers' yeast reduction of 3-(1,3-benzadioxol-5-yl)-6-propoxy-1H-inden-
1-one 4 has been shown to give (S)-3-(1,3-benzodioxol-5-yl)-2,3-dihydro-6-p
ropoxy-1H-indan-1-one 6 in 65% yield with high enantioselectivity (>99.0% e
e), a key intermediate for the synthesis of the endothelin receptor antagon
ist SE 217242, In addition, the substituted 3-arylinden-1-ones 10a-e gave e
qually high enantioselectivity for the 3-arylindan-1-one products 13a-e, Me
chanistic studies of the reaction indicate the operative pathway to be an a
symmetric conjugate reduction, wherein the hydride transfer from NAD(P)H oc
curs from the Re-face of the indenone substrate.