Tetrahedron: Asymmetry

Synthesis of chiral 4, 4′-disubstituted 1, 1′-spirobiindane-7, 7′-diols and related phosphoramidites: the substituent effect of SIPHOS ligands in Rh-catalyzed …

SF Zhu, Y Fu, JH Xie, B Liu, L Xing, QL Zhou

Index: Zhu, Shou-Fei; Fu, Yu; Xie, Jian-Hua; Liu, Bin; Xing, Liang; Zhou, Qi-Lin Tetrahedron Asymmetry, 2003 , vol. 14, # 20 p. 3219 - 3224

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Citation Number: 48

Abstract

Three chiral 4, 4′-substituted 1, 1′-spirobiindane-7, 7′-diols and related monodentate spiro phosphoramidite ligands have been readily synthesized from enantiomerically pure 1, 1′-spirobiindane-7, 7′-diol. Excellent enantioselectivities were obtained with these new ligands in the rhodium-catalyzed asymmetric hydrogenation of dehydroamino acid derivatives and enamides. Comparing SIPHOS, ligands 4, 4′-dibromo-SIPHOS and 4, 4 ...