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Beilstein J. Org. Chem. 2018, 14, 373–380, doi:10.3762/bjoc.14.25
Graphical Abstract
Scheme 1: Silicon-mediated Mukaiyama-type aldol reaction of octyl 2-(pentafluoro-λ6-sulfanyl)acetate (1) with ...
Figure 1: Newman projections of the syn- and the anti-diastereomeric aldol addition products.
Scheme 2: Mechanism of the formation of aldol addition products.
Scheme 3: Formation of (E)-configured aldol condensation products.
Scheme 4: Anticipated mechanism of formation of aldol condensation products.
Scheme 5: Synthesis of SF5-substituted acetmorpholide 8.
Scheme 6: Intermediate formation of the (Z)-ketene aminal from morpholide 8 with TMSOTf/ Et3N and subsequent ...
Beilstein J. Org. Chem. 2013, 9, 2688–2695, doi:10.3762/bjoc.9.305
Scheme 1: Sequential CEYM–Diels–Alder reaction.
Scheme 2: One-pot CM–Diels–Alder reaction with fluorinated alkyne 1a.
Beilstein J. Org. Chem. 2008, 4, No. 12, doi:10.3762/bjoc.4.12
Figure 1: Natural sphingosines 1a, 2a and synthesized fluorinated analogues 1b, 2b.
Scheme 1: Synthesis of 4-fluorosphingosine (2b); Reagents: i ClTi(OEt)3/Et3N, CH2Cl2, 13 h, 0 °C; ii 15% aq c...
Scheme 2: Mechanism of the aldol reaction.
Figure 2: Favorable conformations of the tert-butyl amino acid ester 7.
Figure 3: π–A Isotherms of ceramide (2a) and 4-fluoroceramide (2b) at 20 °C (80 cm2/min compression velocity)....
Figure 4: Cycles of compression and expansion for ceramide (2a) and 4-fluoroceramide (2b).