ChemInform Abstract: Chiral Enhancement in Diethyl Malonate Addition by Morphosynthesized L‐Proline Mesoporous Silica.

Prasetyanto, Eko Adi; Lee, Seung‐Cheol; Jeong, Sung-Min; Park, Sang‐Eon

doi:10.1002/chin.200833029

Cited by 1 publication

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“…Then L-proline functionalized mesoporous silica was employed as the catalyst under the same reaction conditions (i.e., piperidine in dichloromethane) in the asymmetric diethyl malonate addition reaction to cyclohex-2-en-1-one: 7.5% L-proline vs. silica molar ratio was found to give the best result (61% conversion, 70% ee) at 40 °C. Interestingly, the L-proline functionalized mesoporous silica could be reused many times without losing significant stereoselectivity and can be easily recovered being in heterogeneous phase [29].…”

Section: Malonates and Related 13-dicarbonylsmentioning

confidence: 99%

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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: Malonates and Related 13-dicarbonylsmentioning

confidence: 99%

“…Other details of this reaction will be described later. Now most of the instances of cyclopropanation in order to form bicyclo[n.1.0]alkanes are carried out by bromonitromethane (29).…”

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confidence: 99%