TY  - JOUR
A1  - Schmidt, Bernd
A1  - Staude, Lucia
A1  - Kelling, Alexandra
A1  - Schilde, Uwe
T1  - A Cross-Metathesis-Conjugate addition route to enantiopure gamma-Butyrolactams and gamma-Lactones from a C-2-Symmetric Precursor
JF  - European journal of organic chemistry
N2  - A protected derivative of (3R, 4R)-hexa-1,5-diene-3,4-diol, a conveniently accessible C-2-symmetric building block, undergoes single or double cross metathesis with methyl acryl-ate. The cross metathesis products are amenable to stereoselective conjugate addition reactions and can be converted into either gamma-butyrolactones or gamma-lactams.
KW  - Lactams
KW  - Lactones
KW  - Oxygen heterocycles
KW  - Metathesis
KW  - Desymmetrization
Y1  - 2011
U6  - https://doi.org/10.1002/ejoc.201001528
SN  - 1434-193X
IS  - 9
SP  - 1721
EP  - 1727
PB  - Wiley-Blackwell
CY  - Malden
ER  - 
TY  - JOUR
A1  - Yin, Jian
A1  - Linker, Torsten
T1  - Stereoselective diversity-oriented syntheses of functionalized saccharides from bicyclic carbohydrate 1,2-lactones
JF  - Tetrahedron
N2  - Bicyclic carbohydrate 1,2-lactones have been synthesized in only two steps and high yields by saponification and subsequent cyclization from known malonate addition products to glycals. The gluco-configured lactone serves as an important precursor for diversity-oriented syntheses. Thus, stereoselective opening of the lactone ring was realized with various nucleophiles in the presence of Sc(OTf)(3). This enabled the introduction of different substituents at the anomeric position, to afford a broad variety of 1-functionalized carbohydrates. On the other hand, stereoselective alpha-substitution of the gluco-configured lactone with different electrophiles and subsequent ring opening gives a collection of 2-functionalized saccharides. More than 30 products have been isolated in analytically pure form, and their configurations were unequivocally established by various NMR methods. Thus, carbohydrate 1,2-lactones are attractive precursors for the stereoselective synthesis of diverse saccharides.
KW  - Carbohydrates
KW  - Lactones
KW  - Glycosides
KW  - Molecular diversity
KW  - Synthetic methods
Y1  - 2011
U6  - https://doi.org/10.1016/j.tet.2011.01.069
SN  - 0040-4020
VL  - 67
IS  - 13
SP  - 2447
EP  - 2461
PB  - Elsevier
CY  - Oxford
ER  - 
TY  - JOUR
A1  - Schmidt, Bernd
A1  - Geissler, Diana
T1  - Olefin-Metathesis-Based Synthesis of Furans by an RCM/Deprotonation/Phosphorylation Sequence and Their Diels-Alder Reactions
JF  - European journal of organic chemistry
N2  - Butenolides, obtained by ring-closing metathesis (RCM) of acrylates, undergo quantitative deprotonation with amide bases. Trapping of the resulting anions with electrophiles, for example, chlorophosphates, give furans. Subsequent DielsAlder reaction and acid-catalysed rearrangement of the resulting oxabicyclonorbornadienes give substituted benzenes.
KW  - Lactones
KW  - Metathesis
KW  - Ruthenium
KW  - Oxygen heterocycles
KW  - Metalation
Y1  - 2011
U6  - https://doi.org/10.1002/ejoc.201101078
SN  - 1434-193X
IS  - 35
SP  - 7140
EP  - 7147
PB  - Wiley-VCH
CY  - Weinheim
ER  -