31280-60-1Relevant articles and documents
Asymmetric reduction of aliphatic ketones and acyl silanes using chiral anti-pentane-2,4-diol and a catalytic amount of 2,4-dinitrobenzenesulfonic acid
Matsuo, Jun-Ichi,Hattori, Yu,Hashizume, Mio,Ishibashi, Hiroyuki
experimental part, p. 6062 - 6069 (2010/10/02)
Aliphatic ketones were reduced to the corresponding secondary alcohols by using anti-1,3-diol and a catalytic amount of 2,4-dinitrobenzenesulfonic acid (DNBSA) in benzene at reflux. Addition of 1-octanethiol in that media improved the efficiency of the reduction. Asymmetric reduction of aliphatic ketones was performed by using chiral anti-pentane-2,4-diol, and highly asymmetric induction (up to >99% ee) was observed in the reduction of tert-alkyl ketones. Asymmetric reduction of acyl silanes using chiral anti-pentane-2,4-diol and DNBSA proceeded efficiently in the absence of octanethiol and the corresponding α-silyl alcohols were obtained in high yields with high ees.
Optically pure α-(trimethylsilyl)benzyl alcohol: A practical chiral auxiliary for oxocarbenium ion reactions
Cossrow, Jennifer,Rychnovsky, Scott D.
, p. 147 - 150 (2007/10/03)
(matrix presented) Enantiopure (S)-α-(trimethylsilyl)benzyl alcohol (98% ee) was prepared by Noyori's transfer hydrogenation of benzoyltrimethylsilane. The corresponding trimethylsilyl ether was subjected to Marko's silyl modified Sakurai conditions with
Enantioselective synthesis of a-hydroxysilanes by bioreduction of aroyltrimcthylsilanes
Patrocinio, Amauri F.,Correa Jr., Ivan R.,Moran, Paulo J. S.
, p. 3133 - 3137 (2007/10/03)
Aromatic acylsilanes [Ar-CO-SiMe3; Ar = C6H5,4-ClC6H4, 2-, 3- and 4-OMeC6H4, 3,4-(OMe)2C6H3 and 3,4-OCH2OC6H3] were reduced by baker's yeast to optically active a-silyl alcohols in 20-70% yield and 43-88% ee. Comments are made on the influence of silicon in this bioreduction reaction. The Royal Society of Chemistry 1999.