99339-63-6Relevant academic research and scientific papers
Catalytic asymmetric cyanosilylation of ketones with chiral Lewis base
Tian, Shi-Kai,Hong, Ran,Deng, Li
, p. 9900 - 9901 (2007/10/03)
The development of broadly applicable and practical catalytic approaches for the enantioselective creation of quaternary stereocenters remains a highly desirable yet challenging goal. In this Communication, we describe a highly enantioselective cyanosilylation of acetal ketones (α,α-dialkoxy ketones) catalyzed by modified cinchona alkaloids. This reaction is the first highly enantioselective cyanosilylation of ketones catalyzed by an organic chiral Lewis base and is found to be highly efficient with acetal ketones bearing a broad range of alkyl, aryl, alkenyl, and alkynyl substituents. This new catalytic asymmetric reaction, coupled with the versatility of the acetal functionality, provides a broadly useful synthetic method for chiral building blocks bearing quaternary stereocenters. Acetal ketones, readily accessible but previously unexplored in asymmetric synthesis, demonstrate unusual reactivity and selectivity toward the nucleophilic cyanosilylation, thereby suggesting that they may be interesting substrates for other catalytic enantioselective reactions. Copyright
Catalytic asymmetric cyanosilylation of ketones, aldehydes, thioketones, thioaldehydes, imines and hydrazones
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Page 10, (2008/06/13)
One aspect of the present invention relates to a method for the catalytic asymmetric cyanosilylation of ketones, aldehydes, thioketones, thioaldehydes, imines and hydrazones. The critical elements of the method are: a non-racemic chiral tertiary-amine-con
α,α-DIALKOXYARYL KETONES AND RELATED COMPOUNDS I. REACTION OF PHENYLGLYOXAL WITH PRIMARY ALCOHOLS IN AN ACIDIC MEDIUM
Mizyuk, V. L.,Kinakh, V. G.,Lapshin, A. V.,Kharchevnikov, A. P.,Shibanov, V. V.
, p. 570 - 577 (2007/10/02)
The reaction of phenylglyoxal with a series of primary alcohols in the presence of catalytic amounts of sulfuric acid in boiling benzene was studied.Of the three possible reaction products (keto acetal, aldehydo ketal, and acetal ketal) only the first is
