Detail of "260354-12-9"

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In situ preparation of chiral compounds derived from oxazaborolidine-borane complexes and their use as catalysts in asymmetric reductions of ketones and ether oximes

In situ preparation of chiral compounds derived from oxazaborolidine-borane complexes and their use as catalysts in asymmetric reductions of ketones and ether oximes. Burgos, Alain; Bertrand, Blandine; Frein, Stephane; Pluvie, Jean Francois; Roussiasse, Sonia (PPG-Sipsy, Fr.). There are some commonly used reagents like 260354-12-9 in this article. Fr. Demande FR 2860794 A1 15 Apr 2005, 30 pp. (French). (France). CODEN: FRXXBL. CLASS: ICM: C07F005-04. APPLICATION: FR 2003-11838 9 Oct 2003. DOCUMENT TYPE: Patent CA Section: 27 (Heterocyclic Compounds (One Hetero Atom)) Section cross-reference(s): 29, 45 The invention is related to the in situ prepn. of chiral compds. derived from oxazaborolidine-borane complexes by reacting a metal borohydride with a Lewis base, and an ester of an inorg. acid, followed by addn. of an optically active amino-alc. and to their use in the prepn. of chiral alcs. and ketones by asym. redn. of prochiral ketones and ether oximes. The method eliminates the use of I2 in the prepn. of the oxazaborolidine-borane complex. Thus, NaBH4 in THF was mixed with PhNEt2, the mixt. cooled to 5°, Me2SO4 added and the mixt. stirred at 20° for 1 h, and finally mixed with (R)-diphenylprolinol at 20° for 1 h. A soln. of 3-chloro-1-(2-thienyl)propanone in THF was added to the above preheated mixt. over a period of 1.5 h, followed by hydrolysis for 1 h at 20° to give the corresponding alc. in high chem. purity. .