ChemInform Abstract: Asymmetric Catalytic Aziridination of Cyclic Enones.

Vincentiis, Francesco De; Bencivenni, Giorgio; Pesciaioli, Fabio; Mazzanti, Andrea; Bartoli, Giuseppe; Galzerano, Patrizia; Melchiorre, Paolo

doi:10.1002/chin.201043096

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“…The authors claim the most interesting feature of this reaction is that, conversely from most of the reactions described in this review, the catalytic couple is not formed by an amine and an acid, but by two amines. A couple between a Cinchona alkaloid derivative and an aminoacid has already been used by other research groups and examples have also been reported in this review, too [63,81,85,86]. However, in previous reports, Cinchona alkaloid derivatives act as the catalysts and drive the enantioselectivity, whereas aminoacid sometimes improves the general efficiency of the catalyst trough matched/mismatched combinations.…”

Section: Diels-aldermentioning

confidence: 84%

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Asymmetric Organocatalytic Reactions of α,β-Unsaturated Cyclic Ketones

2011

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Abstract: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 years. At the same time, asymmetric Diels-Alder reactions have been developed and often a mechanism has been demonstrated to be a double addition rather than synchronous. This review aims to cover literature up to the end of 2010, describing all the different organocatalytic asymmetric 1,4-conjugate additions even if they are listed as transfer hydrogenation, cycloadditions or desymmetrization of aromatic compounds.

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Section: Diels-aldermentioning

confidence: 84%

“…Moreover, the catalyst for the reaction is an amino acid-Cinchona alkaloid salt and both the pseudo-enantiomers of the catalyst (73 and 73', the same as 56 with different counterions) are available, so both optical antipodes of the aziridine can be prepared (Scheme 21) [85,86].…”

Section: Scheme 17mentioning

confidence: 99%