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2005
Enantioselective syntheses
O 0031
Influences of Electronic Effects and Anions on the Enantioselectivity in the
Asymmetric Borane Reduction of Ketones. — It is
06- 039 Oxazaborolidine-Catalyzed
found that electronic effects have an obvious influence on the enantioselectivity of the
reduction. Electron-donating substituents in the ketones increase the enantioselectivity,
whereas electron-withdrawing groups lead to a decrease. The enantioselectivity can
also be improved by tuning the electronic effect of catalyst. Additionally, it is found
that soluble and coordination-able anions strongly affect the stereoselectivity, especially for the methoxy catalyst (Ib). — (XU*, J.; WEI, T.; ZHANG, Q.; J. Org. Chem. 69
(2004) 20, 6860-6866; Key Lab. Bioorg. Chem. Mol. Eng. Minist. Educ., Coll. Chem.
Mol. Eng., Peking Univ., Beijing 100871, Peop. Rep. China; Eng.) — Jannicke
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