TY  - JOUR
A1  - Schmidt, Bernd
A1  - Riemer, Martin
A1  - Schilde, Uwe
T1  - Tandem Claisen Rearrangement/6-endo Cyclization Approach to Allylated and Prenylated Chromones
JF  - European journal of organic chemistry
N2  - Allyl, dimethylallyl and prenyl ethers derived from o-acyl-phenols reacted upon microwave irradiation to form C-allylated or -prenylated chromone derivatives, depending on the substitution pattern of the arene and the allyl substituent. The reaction proceeds through a tandem Claisen rearrangement and 6-endo-trig or 6-endo-dig cyclization sequence. For prenyl ethers, the tandem sequence can be extended by a Cope rearrangement to furnish 6-prenylchromones. The method is potentially useful for the synthesis of natural products and drugs.
KW  - Allylic compounds
KW  - Arenes
KW  - Oxygen heterocycles
KW  - Microwave chemistry
KW  - Rearrangement
KW  - Michael addition
Y1  - 2015
U6  - https://doi.org/10.1002/ejoc.201501151
SN  - 1434-193X
SN  - 1099-0690
IS  - 34
SP  - 7602
EP  - 7611
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  -