TY  - JOUR
A1  - Schultze, Christiane
A1  - Foß, Stefan
A1  - Schmidt, Bernd
T1  - 8-Prenylflavanones through microwave promoted tandem claisen rearrangement/6-endo-trig cyclization and cross metathesis
JF  - European journal of organic chemistry
N2  - Prenylated flavanones were obtained from ortho-allyloxy chalcones through a one-pot sequence of Claisen rearrangement and 6-endo-trig cyclization, followed by olefin cross metathesis of the intermediate allyl flavanones with 2-methyl-2-butene. The synthetic utility of this route is illustrated for the synthesis of several naturally occurring prenyl flavanones.
KW  - tandem reactions
KW  - arenes
KW  - oxygen heterocycles
KW  - microwave chemistry
KW  - rearrangement
Y1  - 2020
U6  - https://doi.org/10.1002/ejoc.202001378
SN  - 1434-193X
SN  - 1099-0690
VL  - 2020
IS  - 47
SP  - 7373
EP  - 7384
PB  - Wiley-VCH
CY  - Weinheim
ER  - 
TY  - JOUR
A1  - Umbreen, Sumaira
A1  - Linker, Torsten
T1  - Simple Synthesis of Conformationally Fixed Glycosamine Analogues by Beckmann Rearrangement at the Carbohydrate Ring
JF  - Chemistry - a European journal
N2  - Conformationally fixed carbohydrate analogues are promising small-molecule inhibitors for hydrolases like O-GlcNAcase (OGA); however, their synthesis usually requires many steps. Herein we describe cycloadditions of dichloroketene to various glycals and subsequent Beckmann rearrangements, which offer an easy and stereoselective entry to glycosamine derivatives in good yields. The reactions are applicable for hexoses, pentoses, and disaccharides, and transformations to the corresponding imidates proceed smoothly. First biological tests reveal that such imidates indeed inhibit human OGA.
KW  - carbohydrates
KW  - cycloaddition
KW  - enzyme inhibitors
KW  - rearrangement
KW  - selective syntheses
Y1  - 2015
U6  - https://doi.org/10.1002/chem.201406546
SN  - 0947-6539
SN  - 1521-3765
VL  - 21
IS  - 20
SP  - 7340
EP  - 7344
PB  - Wiley-VCH
CY  - Weinheim
ER  - 
TY  - JOUR
A1  - Schmidt, Bernd
A1  - Riemer, Martin
A1  - Schilde, Uwe
T1  - Chroman-4-ones via microwave-promoted domino claisen rearrangement-oxa-michael addition: Synthesis of tabchromones A and B
JF  - Synlett : accounts and rapid communications in synthetic organic chemistry
N2  - Allyl phenyl ethers with a pendant enone substituent undergo, upon microwave irradiation, a domino sequence of Claisen rearrangement and 6-endo-trig-cyclization to furnish functionalized chroman-4-ones. The natural products tabchromones A and B were synthesized via this method.
KW  - cyclization
KW  - Michael addition
KW  - rearrangement
KW  - tandem reaction
KW  - Wacker reaction
Y1  - 2014
U6  - https://doi.org/10.1055/s-0034-1379364
SN  - 0936-5214
SN  - 1437-2096
VL  - 25
IS  - 20
SP  - 2943
EP  - 2946
PB  - Thieme
CY  - Stuttgart
ER  -