2008
DOI: 10.1038/nature07370
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Natural products as inspiration for the development of asymmetric catalysis

Abstract: Biologically active natural products often contain particularly challenging structural features and functionalities. Perhaps foremost among these difficulties are issues of stereochemistry. A useful strategy for synthesizing these molecules is to devise novel methods of bond-formation that provide new opportunities for enantioselective catalysis. In using this tactic, target structures define the problems to be solved and ultimately drive development of catalysis forward. New enantioselective methods discovere… Show more

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Cited by 229 publications
(100 citation statements)
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“…Such interactions are ubiquitous in enzymes [18] and have been successfully engineered into homogeneous catalysts through, for example, the modification of porphyrin with aromatic ligands [19,20]. Recently, manipulation of these interactions has garnered significant interest for the development of ''biomimetic'' heterogeneous catalysts for a variety of reactions [21][22][23][24].…”
Section: Introductionmentioning
confidence: 98%
“…Such interactions are ubiquitous in enzymes [18] and have been successfully engineered into homogeneous catalysts through, for example, the modification of porphyrin with aromatic ligands [19,20]. Recently, manipulation of these interactions has garnered significant interest for the development of ''biomimetic'' heterogeneous catalysts for a variety of reactions [21][22][23][24].…”
Section: Introductionmentioning
confidence: 98%
“…These compounds have potential medicinal interest, owing to the unique biological activities of such natural products. [7] Typically, construction of 3-(a-hydroxy-b-carbonyl) oxindoles is attractive and imperative because several pharmaceutical candidates, taking surugatoxin, for instance, [8] contain this structural motif. The direct catalytic asymmetric aldol reaction [9] is a powerful and atom-economical method for the synthesis of such oxindoles.…”
Section: Introductionmentioning
confidence: 99%
“…[18] The concept of spatial orientation requires that the orientation of the starting compound is fixed in space, as depicted schematically in Figure 1. If reagent 4 reacts from the left with the central carbon atom, then the resulting structure with a central stereogenic sp 3 carbon atom will be the mirror image of the structure obtained when reagent 4 reacts from the right. The successful implementation of this [*] Prof. A. Kuhn [+] approach for asymmetric synthesis not only requires that the prochiral molecules are prevented from tumbling in space during exposure to the reactant, but also that all molecules in the ensemble have a fixed orientation with respect to one another, so that they give the product with the same handedness.…”
mentioning
confidence: 98%
“…The selective synthesis of only one of the two mirror-image forms of a chiral molecule is therefore of major importance. Although great progress has been made in chemical and biochemical asymmetric synthesis, [2,3] only a few systems permit absolute asymmetric synthesis, that is, enantioselective synthesis from achiral starting materials without the help of chiral reagents or catalysts. [4,5] Absolute means of inducing appreciable handedness are, for example, photochemical reactions with circularly polarized light, [6][7][8] synthesis in noncentrosymmetric or enantiomorphic crystals, [9,10] reactions in crystals with reduced symmetry as a result of the mixing of different compounds, [11,12] autocatalytic amplification of a chiral bias resulting from small random fluctuations, [13,14] aggregation in supramolecular assemblies, [15] or recrystallization under special conditions.…”
mentioning
confidence: 99%