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Beilstein J. Org. Chem. 2011, 7, 1189–1197, doi:10.3762/bjoc.7.138
Graphical Abstract
Scheme 1: Proposed catalytic cycle of the lithium phosphonate catalyzed cross benzoin coupling [18].
Scheme 2: Phosphonate as precatalysts in benzoin coupling [18,26].
Scheme 3: Synthesis of diols 1–4, 6–7; diol 5 is commercially available.
Figure 1: X-ray crystal structure of 6. (M)-(S,S) and (P)-(R,R) pair of enantiomers; intermolecular O1–O2 dis...
Figure 2: X-ray crystal structure of 7. (M)-(S,S) and (P)-(R,R) pair of enantiomers; intermolecular O1–O2 dis...
Scheme 4: Synthesis of phosphonates 9–15.
Figure 3: 31P NMR of phosphonate 14 (a) and 15 (b).
Figure 4: X-ray crystal structure of 15. (M)-(R,S) diastereomer; ellipsoids correspond to 50% probability lev...
Scheme 5: Lithium phosphonate catalysts in cross benzoin coupling.
Figure 5: Phosphonate precatalysts 9–15 in cross benzoin coupling.