74572-10-4Relevant academic research and scientific papers
Stereoselective synthesis of c-substituted morpholine derivatives using reductive etherification reaction: Total synthesis of chelonin C
Gharpure, Santosh J.,Prasad
experimental part, p. 10325 - 10331 (2012/01/31)
A general strategy is developed for the stereoselective synthesis of C-substituted morpholine derivatives using intramolecular reductive etherification reaction. The method is extended to the first stereoselective total synthesis of (±)-chelonin C.
Chirality transfer in Au-catalyzed cyclization reactions of monoallylic diols: Selective access to specific enantiomers based on olefin geometry
Aponick, Aaron,Biannic, Berenger
supporting information; experimental part, p. 1330 - 1333 (2011/05/15)
The gold(I)-catalyzed cyclization of monoallylic diols to form tetrahydropyrans is shown to be highly stereoselective when chiral allylic alcohols are employed. Substrates that differ only in olefin geometry provide enantiomeric products from formal SN2′ reactions in high yields with excellent chirality transfer. The allylic alcohol stereochemistry also efficiently controls the facial selectivity when the substrates include additional stereocenters.
DIBENZOTHIOPHENE DERIVATIVES AS DNA- PK INHIBITORS
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Page/Page column 84-85, (2010/12/26)
Compound formula I: wherein: X1 and X2 may be either (a) C and O, (b) N and N, or (c) C and NH, where the dotted bonds represents a double bond in the appropriate location; R1 and R2 are independently selected from hydrogen, an optionally substituted C1-7 alkyl group, an optionally substituted C3-20 heterocyclyl group, or an optionally substituted C5-20 aryl group, or may together form, along with the nitrogen atom to which they are attached, an optionally substituted heterocyclic ring having from 4 to 8 ring atoms; RN1 is selected from hydrogen and an optionally substituted C1-4 alkyl group; RC1 is selected from an optionally substituted C1-7 alkyl group, an optionally substituted C3-20 heterocyclyl group, or an optionally substituted C5-20 aryl group; or RN1 and RC1 may together form an optionally substituted C2-4 alkylene group.
Diastereoselective synthesis of enantiopure morphelines by electrophilic selenium-induced 6-exo cyclizations on chiral 3-allyl-2-hydroxymethylperhydro-1, 3-benzoxazine derivatives
Pedrosa, Rafael,Andres, Celia,Mendiguchia, Pilar,Nieto, Javier
, p. 8854 - 8863 (2007/10/03)
Enantiopure morpholine derivatives have been prepared by selenocyclofunctionalization of chiral 3-allyl-2-hydroxymethyl-substituted perhydro-1,3-benzoxazine derivatives. The cyclization occurs in high yields and diastereoselection, although the temperature of the reaction and the structure of the substituent at C-2 and the substitution pattern of the double bond can modify the regio- and stereochemistry of the final products.
SYNTHESIS AND ABSOLUTE CONFIGURATION OF SUBSTITUTED MORPHOLINES
Bettoni, Giancarlo,Franchini, Carlo,Perrone, Roberto,Tortorella, Vincenzo
, p. 409 - 415 (2007/10/02)
We studied methods of stereospecific synthesis that enabled us to obtain variously substituted morpholinic compounds and to determine their absolute configuration.From a study of the chiroptical properties of synthetic N-(2-pyridyl-N-oxide) derivatives of optically active morpholines, it was possible to correlate the sign of the Cotton effect with the absolute configuration.This correlation agrees with that previously established for derivatives of the piperidine type.By evaluating the various contributions to the Cotton effect of substituents in positions 2 and 3, we established the absolute configuration of bicyclic compounds condensed in the two positions mentioned above.
