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Beilstein J. Org. Chem. 2020, 16, 88–105, doi:10.3762/bjoc.16.11
Graphical Abstract
Scheme 1: Arbusov, phospha-Fries, and phospha-Brook rearrangements.
Scheme 2: Cyclization of 1a and 1b under acidic conditions.
Scheme 3: The synthesis of P-stereogenic β-hydroxyalkylphosphine sulfides.
Scheme 4: Cyclization of 8 and 19 in the presence of H3PO4.
Scheme 5: Cyclization of (SP)-19 in the presence of H3PO4.
Figure 1: 1H NMR spectra of compounds 12 and 29.
Figure 2: 13C NMR spectra of compounds 12 and 29.
Scheme 6: Synthesis of the alkenylphosphine sulfides used in study.
Scheme 7: The reaction of mesylate compounds with Lewis-acidic AlCl3.
Scheme 8: The reaction of alkenylphosphine sulfides with AlCl3.
Scheme 9: Rearrangement of 20 in the presence of Brønsted acid. The calculated energies next to the arrows ar...
Scheme 10: Rearrangement of 20 in the presence of Lewis acid. The calculated energies next to the arrows are r...
Scheme 11: The synthesis of chiral substrates for rearrangement reactions.
Scheme 12: The reaction of (SP)-60 and (SP)-65 with AlCl3.
Scheme 13: Reaction of chiral β-hydroxyalkylphosphine sulfides with Brønsted acid.
Scheme 14: Attempted cyclization of enantiomerically enriched 53 and 46.