TY  - JOUR
A1  - Schmidt, Bernd
A1  - Hauke, Sylvia
T1  - Olefin cross metathesis based de novo synthesis of a partially protected L-amicetose and a fully protected L-cinerulose derivative
JF  - Beilstein journal of organic chemistry
N2  - Cross metathesis of a lactate derived allylic alcohol and acrolein is the entry point to a de novo synthesis of 4-benzoate protected L-amicetose and a cinerulose derivative protected at C5 and C1.
KW  - carbohydrates
KW  - de novo synthesis
KW  - lactate
KW  - metathesis
KW  - ruthenium
Y1  - 2014
U6  - https://doi.org/10.3762/bjoc.10.102
SN  - 1860-5397
VL  - 10
SP  - 1023
EP  - 1031
PB  - Beilstein-Institut zur Förderung der Chemischen Wissenschaften
CY  - Frankfurt, Main
ER  - 
TY  - JOUR
A1  - Schmidt, Bernd
A1  - Hauke, Sylvia
T1  - Metathesis-Based de novo synthesis of noviose
JF  - European journal of organic chemistry
N2  - The rare carbohydrate L-(+)-noviose was synthesized from enantiomerically pure L-lactate. The configuration at C-4 was established by diastereoselective nucleophilic addition to an in-situ-generated lactaldehyde. The resulting homoallylic alcohol was further transformed into a set of ring-closing metathesis (RCM) precursors. These compounds were converted into noviose in few steps using RCM and RCM-allylic-oxidation sequences.
KW  - Carbohydrates
KW  - Allylic oxidation
KW  - Oxygen heterocycles
KW  - Metathesis
KW  - Ruthenium
Y1  - 2014
U6  - https://doi.org/10.1002/ejoc.201301615
SN  - 1434-193X
SN  - 1099-0690
VL  - 2014
IS  - 9
SP  - 1951
EP  - 1960
PB  - Wiley-VCH
CY  - Weinheim
ER  - 
TY  - JOUR
A1  - Schmidt, Bernd
A1  - Hauke, Sylvia
A1  - Muehlenberg, Nino
T1  - Imino glycals via Ruthenium-catalyzed RCM and isomerization
JF  - Synthesis
N2  - N-Allyl-N-homoallylamines were converted in one step into cyclic enamides via a ruthenium-catalyzed assisted tandem catalytic ring-closing metathesis-isomerization sequence. The sequence relies on the in situ transformation of a metathesis active Ru-carbene into an isomerization active Ru-hydride by addition of hydroxide as a chemical trigger.
KW  - heterocycles
KW  - isomerization
KW  - metathesis
KW  - ruthenium
KW  - tandem reaction
Y1  - 2014
U6  - https://doi.org/10.1055/s-0033-1338615
SN  - 0039-7881
SN  - 1437-210X
VL  - 46
IS  - 12
SP  - 1648
EP  - 1658
PB  - Thieme
CY  - Stuttgart
ER  - 
TY  - JOUR
A1  - Schmidt, Bernd
A1  - Hauke, Sylvia
T1  - Cross metathesis of allyl alcohols: how to suppress and how to promote double bond isomerization
N2  - Under standard conditions the cross metathesis of allyl alcohols and methyl acrylate is accompanied by the formation of ketones, resulting from uncontrolled and undesired double bond isomerization. By conducting the CM in the presence of phenol, the catalyst loading and the reaction time required for quantiative conversion can be reduced, and isomerization can be suppressed. On the other hand, consecutive isomerization can be deliberately promoted by evaporating excess methyl acrylate after completing cross metathesis and by adding a base or silane as chemical triggers.
Y1  - 2014
UR  - http://pubs.rsc.org/en/content/articlepdf/2013/ob/c3ob40167g
U6  - https://doi.org/10.1039/c3ob40167g
SN  - 1477-0520
ER  -