Enantioselective Organocatalytic α-Fluorination of Cyclic Ketones
نویسندگان
چکیده
منابع مشابه
Enantioselective organocatalytic α-fluorination of cyclic ketones.
The first highly enantioselective α-fluorination of ketones using organocatalysis has been accomplished. The long-standing problem of enantioselective ketone α-fluorination via enamine activation has been overcome via high-throughput evaluation of a new library of amine catalysts. The optimal system, a primary amine functionalized Cinchona alkaloid, allows the direct and asymmetric α-fluorinati...
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The 1,4-conjugate addition of nucleophiles to α,β-unsaturated carbonyl compounds represents one fundamental bond-forming reaction in organic synthesis. The development of effective organocatalysts for the enantioselective conjugate addition of malonate, nitroalkane and other carbon and heteroatom nucleophiles to cycloenones constitutes an important research field and has been explored in recent...
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Despite the fact that only 21 fluorinated molecules are known to be biosynthesized, it is notable that about 20–25% of all modern pharmaceuticals and agrochemicals incorporate at least one fluorine atom. Nevertheless, the practice of introducing fluorine atoms into bioactive compounds is rather recent, as the first synthetic fluorinated drug, namely 5-fluorouracil, was synthesized as late as in...
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An enantioselective Michael addition of ketones to alkylidenemalononitriles catalyzed by chiral primary amine I with (R)-5c as a co-catalyst in good yields (>90%) and with good enantioselectivities (85-96% ee) has been developed. The strategy has also been extended to a three-component version through a domino Knoevenagel/Michael sequence with similar or better outcomes.
متن کاملOrganocatalytic asymmetric fluorination of α-chloroaldehydes involving kinetic resolution
In a previous study it was shown that the enantioselective α-fluorination of racemic α-chloroaldehydes with a chiral organocatalyst yielded the corresponding α-chloro-α-fluoroaldehydes with high enantioselectivity. It was also revealed that kinetic resolution of the starting aldehydes was involved in this asymmetric fluorination. This paper describes the determination of the absolute stereochem...
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ژورنال
عنوان ژورنال: Journal of the American Chemical Society
سال: 2011
ISSN: 0002-7863,1520-5126
DOI: 10.1021/ja111163u