01522nas a2200229 4500008004100000022001400041245014000055210006900195260007700264300001000341490000600351520062400357653001900981653001801000653001901018653001601037653004501053100001901098700002301117700002101140856013101161 2012 eng d a2193-580700aDimethyl [(2R,3R,5S)-5-phenylmorpholine-2,3-diyl]diacetate as a designer substrate in the syntheses of important heterocyclic scaffolds0 aDimethyl 2R3R5S5phenylmorpholine23diyldiacetate as a designer su aBOSCHSTRASSE 12, D-69469 WEINHEIM, GERMANYbWILEY-V C H VERLAG GMBHcSEP a65-700 v13 a
Designed scaffold dimethyl [(2R,3R,5S)-5-phenylmorpholine-2,3-diyl]diacetate was synthesized in optically pure form by photoinduced one-electron reductive beta-activation of an alpha,beta-unsaturated carbonyl moiety for stereoselective C-C bond formation. Use of the morpholine derivative as a ``chemical multitalent'' is demonstrated by its easy transformation to valuable heterocyclic building blocks such as methyl [(2R,3S)-3-hydroxy-5-oxopyrrolidin-2-yl]acetate, methyl [(2R,3S)-3-amino-5-oxotetrahydrofuran-2-yl]acetate, (3R,4S)-4-aminohexane-1,3,6-triol, and 2-[(2R,3S)-3-aminotetrahydrofuran-2-yl]ethanol.
10aAmino alcohols10abutyrolactams10abutyrolactones10amorpholines10aphotoinduced electron transfer reactions1 aPandey, Ganesh1 aGaikwad, Amrut, L.1 aGadre, Smita, R. uhttp://library.ncl.res.in/content/dimethyl-2r3r5s-5-phenylmorpholine-23-diyldiacetate-designer-substrate-syntheses-important-0