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Synthesis of (±)‐Merrilactone A by a Desymmetrization Strategy
Chemistry – A European Journal, 2018AbstractA concise synthesis of (±)‐merrilactone A has been accomplished featuring desymmetrization of a Cs‐symmetric dilactone, RhI‐catalyzed intramolecular hydroacylation of a 4‐alkynal, and TiIII‐mediated reductive radical cyclization of epoxy‐allene.
Wentan Liu, Bo Wang
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Desymmetrization of myo-inositol
Carbohydrate ResearchChemistry and biology of phosphoinositols have been intensely investigated areas of research over the last 4-5 decades due to their involvement in cellular signal transduction pathways. Efficient laboratory synthesis of enantiomeric derivatives of inositols was a central issue since they were required for the delineation of the myo-inositol cycle as ...
Nivedita T, Patil +3 more
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Enantioselective Desymmetrization of Cyclopropenes by Hydroacylation
Journal of the American Chemical Society, 2010We report an enantioselective desymmetrization of cyclopropenes by intermolecular Rh-catalyzed hydroacylation. Cyclopropylketones, bearing quaternary stereocenters, are produced with diastereocontrol (up to >20:1) and excellent enantiomeric excess (up to >99 ee).
Diem H T, Phan +2 more
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Catalytic Desymmetric Dicarbofunctionalization of Unactivated Alkenes
Angewandte Chemie, 2022AbstractThe construction of multi‐stereocenters by a transition metal‐catalyzed cross‐coupling reaction is a major challenge. The catalytic desymmetric functionalization of unactivated alkenes remains largely unexplored. Herein, we disclose ‐a desymmetric dicarbofunctionalization of 1,6‐dienes via a nickel‐catalyzed reductive cross‐coupling reaction ...
Xianqing Wu +6 more
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Desymmetric Partial Reduction of Malonic Esters
Journal of the American Chemical Society, 2022Desymmetrization of easily available disubstituted malonic esters is a rewarding strategy to access structurally diverse quaternary stereocenters. Particularly, asymmetric reduction of malonic esters would generate a functional group with a lower oxidation state than the remaining ester, thus allowing for more chemoselective derivatization.
Pengwei Xu, Shihao Liu, Zhongxing Huang
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Desymmetrization and degree of chirality
Journal of Mathematical Chemistry, 1991Chiral objects, viewed as distorted derivatives of achiral ones, may be represented by points in a configuration space that is spanned by a set of symmetry coordinates derived for the symmetry group of the achiral object of highest symmetry. We propose a measure (d) that quantifies the displacement of the representative point for a chiral object away ...
Thomas P. E. Auf der heyde +2 more
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Enantioselective Desymmetrization of Diynes
European Journal of Organic ChemistryIn the field of asymmetric synthesis, the desymmetrization of prochiral diynes has arisen as a challenging yet effective strategy for the rapid and efficient construction of structurally diverse and complex molecules. This review explores the various methodologies (cycloadditions, cycloisomerizations, and C‐ and X‐ additions) that enable the ...
Anne Boussonnière +2 more
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Catalytic Enantioselective Intermolecular Desymmetrization of Azetidines
Journal of the American Chemical Society, 2015The first catalytic asymmetric desymmetrization of azetidines is disclosed. Despite the low propensity of azetidine ring opening and challenging stereocontrol, smooth intermolecular reactions were realized with excellent efficiency and enantioselectivity.
Wang, Zhaobin +5 more
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Desymmetrization of OD Structures
Kristall und Technik, 1979AbstractIt has been shown that the symmetry and structure of individual OD layers may depend on their actual stacking in a (polytypic) OD structure, leading to significant deviations from the ideal OD symmetry. This phenomenon has been called “desymmetrization of OD structures”; its significance for polytypism and for crystallochemistry is discussed.
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Desymmetrization of 4,6-diprotected myo-inositol
Chemical Communications, 2013The asymmetric desymmetrization of 4,6-diprotected myo-inositol derivatives was achieved by using a bifunctional, readily available nucleophilic catalyst. The orthogonally protected products were obtained in 80-99% yield with 90-99% ee. Such structures serve as potential enantiopure building blocks for the synthesis of myo-inositol phosphates.
Markus B, Lauber +2 more
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