Oxazoline-based organocatalyst for enantioselective strecker reactions: A protocol for the synthesis of levamisole
A chiral oxazoline-based or-ganocatalyst has been found to efficiently catalyze asymmetric Strecker reactions of various aromatic and aliphatic N-benzhydrylimines with trime-thylsilyl cyanide (TMSCN) as a cyanide source at -20°C to give α-aminoni-triles in high yield (96%) with excellent chiral induction (up to 98% ee). DFT calculations have been performed to rationalize the enantioselective formation of the product with the organo-catalyst in these reactions. The organo-catalyst has been characterized by single-crystal X-ray diffraction analysis, as well as by other analytical methods. This protocol has been extended to the synthesis of the pharmaceutically important drug molecule levamisole in high yield and with high enantioselectivity.
Sadhukhan, Arghya,Sahu, Debashis,Ganguly, Bishwajit,Khan, Noor-Ul H.,Kureshy, Rukhsana I.,Abdi, Sayed H.R.,Suresh,Bajaj, Hari C.
supporting information
p. 14224 - 14232
(2013/11/06)
Enantioselective metal-free diamination of styrenes
Metal-free and asymmetric: The first enantioselective diamination of styrenes simply requires a chiral hypervalent iodine(III) reagent as an oxidant and bismesylimide as a nitrogen source (see scheme, Ms=methanesulfonyl). The reaction proceeds under mild conditions and with high enantiomeric excess.
Roeben, Caren,Souto, Jose A.,Gonzalez, Yolanda,Lishchynskyi, Anton,Muniz, Kilian
p. 9478 - 9482
(2011/11/06)
Enantioselective catalytic reductions of ketones with new four membered oxazaborolidines: Application to (S)-tetramisole
Enantioselective catalytic reduction of ketones with both the enantiomers of new four membered oxazaborolidines is described.
Rama Rao,Gurjar,Kaiwar
p. 859 - 862
(2007/10/02)
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