Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 51, Pages 20628-20631Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja311208a
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Funding
- Robert A. Welch Foundation [F-0038]
- NIH NIGMS [R01-GM069445]
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The ruthenium catalyst generated in situ from H2Ru(CO)(PPh3)(3), (S)-SEGPHOS, and a TAD-DOL-derived phosphoric acid promotes butadiene hydro-hydroxyalkylation to form enantiomerically enriched products. Notably, the observed diastereo- and enantioselectivity is the opposite of that observed using BINOL-derived phosphate counterions in combination with (S)-SEGPHOS, the same enantiomer of the chiral ligand. Match/mismatch effects between the chiral ligand and the chiral TADDOL-phosphate counterion are described. For the first time, single-crystal X-ray diffraction data for a ruthenium complex modified by a chiral phosphate counterion are reported.
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