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Beilstein J. Org. Chem. 2022, 18, 1195–1202, doi:10.3762/bjoc.18.124
Beilstein J. Org. Chem. 2021, 17, 2629–2641, doi:10.3762/bjoc.17.176
Graphical Abstract
Figure 1: Catalyst design principles.
Scheme 1: Synthesis of isothiocyanate 3a and isocyanate 3b.
Scheme 2: Synthesis of sulfinylthioureas C1 and ureas C2.
Scheme 3: Synthesis of adducts 8a,d,f in solution.
Figure 2: DFT-calculated (PBEh-3c/def2-SV(P)//M06-2X/def2-TZVP) structures of catalyst (S,R) and (S,S)-C2, en...
Figure 3: a) Arrangements of reactants in the transition states; b) DFT-calculated (PBEh-3c/def2-SV(P)//M06-2...
Figure 4: DFT-calculated (PBEh-3c/def2-SV(P)//M06-2X/def2-TZVP) reaction profile for the Michael addition of ...
Beilstein J. Org. Chem. 2019, 15, 2948–2957, doi:10.3762/bjoc.15.290
Scheme 1: Ireland–Claisen rearrangement of allyl esters 1a–c.
Scheme 2: Ireland–Claisen rearrangement of 1c mediated by tertiary amines.
Figure 1: Organocatalysts used in this study. Conditions: typical procedure: 1. Et3N (4.9 equiv), DCM, −60 °C...
Scheme 3: Solvent-free Ireland–Claisen rearrangement of cinnamyl esters.
Figure 2: ωB97X-D/6-31G* calculated uncatalyzed Ireland–Claisen rearrangement of 1c. Charges on allylic oxyge...
Figure 3: ωB97X-D/6-31G* calculated Schreiner thiourea (12)-catalyzed Ireland–Claisen rearrangement of 1c. Ch...
Figure 4: ωB97X-D/6-31G* calculated Ph-thiourea (top) and squaramide-catalyzed (bottom) Ireland–Claisen rearr...
Figure 5: a) Rate of product formation; b) reaction profile without catalyst determined by 1H NMR.