TY  - JOUR
A1  - Schmidt, Bernd
A1  - Staude, Lucia
T1  - Desymmetrization of (R,R)-Hexa-1,5-diene-3,4-diol via Monofunctionallization and Rhodium-Catalyzed Allylic Substitution
T2  - The journal of organic chemistry
N2  - A sequence of selective monoprotection and Rh-catalyzed enantioconservative allylic subEtitution is established as a desymmetrization strategy for C-2-symmetric hexa-1,5-diene-3,4-diol. A benzyl protecting group and ethyl carbonate as a leaving group emerged as the most useful combination with respect to reproducibility, stereoselectivity, and yield: A remarkable deviation from the normally observed regiospecificity of Rh-catalyzed allylic alkylations was observed for unprotected carbonates. In this case, a linear, rather than a branched alkylation product was obtained exclusively.
Y1  - 2011
UR  - https://publishup.uni-potsdam.de/frontdoor/index/index/docId/36935
SN  - 0022-3263
VL  - 76
IS  - 7
SP  - 2220
EP  - 2226
PB  - American Chemical Society
CY  - Washington
ER  -