Aryl-bridged C1-symmetric oxazolinyl sulfoximines are applicable in copper-catalyzed asymmetric Mukaiyama aldol reactions with methyl pyruvate. The resulting alpha-hydroxy esters have been obtained with up to 94% ee in good yields. They contain a quaternary stereogenic center and represent valuable precursors for biologically active molecules.
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C1-symmetric oxazolinyl sulfoximines as ligands in copper-catalyzed asymmetric mukaiyama aldol reactions.
Org Lett
March 2008
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52056 Aachen, Germany.
Aryl-bridged C1-symmetric oxazolinyl sulfoximines are applicable in copper-catalyzed asymmetric Mukaiyama aldol reactions with methyl pyruvate. The resulting alpha-hydroxy esters have been obtained with up to 94% ee in good yields. They contain a quaternary stereogenic center and represent valuable precursors for biologically active molecules.
View Article and Find Full Text PDFShaping and enforcing coordination spheres: the implications of C3 and C1 chirality in the coordination chemistry of 1,1,1-tris(oxazolinyl)ethane ("trisox").
Chemistry
May 2007
Anorganisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.
A key feature of tris(oxazolinyl)ethane ("trisox") ligands, which have shown broad scope in asymmetric catalysis, is the orientation and steric demand of their oxazoline substituents. This, along with the modularity of their synthesis determines their coordination chemistry. The possibility to combine oxazolines, in which the stereogenic centers adjacent to the N-donor atoms have different absolute configuration, whilst retaining their ability to coordinate as tripodal ligands, has been demonstrated by the synthesis of the enantiomerically pure C3-symmetric iPr-trisox(S,S,S) and C1-symmetric iPr-trisox(S,S,R) and their reaction with [Mo(CO)3(NCMe)3] yielding [Mo{iPr-trisox(S,S,S)}(CO)3] (1 a) and [Mo{iPr-trisox(S,S,R)}(CO)3] (1 b), respectively.
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