1991
DOI: 10.1016/s0040-4039(00)92368-2
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3-bromo-2-pyrone: an easily prepared chameleon diene and a synthetic equivalent of 2-pyrone in thermal diels-alder cycloadditions

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Cited by 53 publications
(20 citation statements)
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“…25 These nal examples (45-47) collectively reveal the ability of the method to construct optically active products containing two fully substituted vicinal carbon atoms in a single step. 26 With this body of results in hand, a transition state analysis to account for the stereoselection observed for the process is provided in Fig. 2; here, we have focused in particular on explaining the variations in dr observed based on the structural differences in the two respective partners.…”
Section: Resultsmentioning
confidence: 99%
“…25 These nal examples (45-47) collectively reveal the ability of the method to construct optically active products containing two fully substituted vicinal carbon atoms in a single step. 26 With this body of results in hand, a transition state analysis to account for the stereoselection observed for the process is provided in Fig. 2; here, we have focused in particular on explaining the variations in dr observed based on the structural differences in the two respective partners.…”
Section: Resultsmentioning
confidence: 99%
“…Through reaction of 3-bromo-2-pyrone 125 a with 2,2-dimethyl-1,3-dioxole 132 a and 1,1-dimethoxyethylene 13 a under thermal conditions, lactone 133 was obtained with good endo-selectivity,w hereas lactone 134 was achieved with excellent regioselectivity,a ss hown in Scheme 30. [41] Ta ndem Diels-Alder reactions have attracted much synthetic attentioni nt he past decades because of their powerful potential to rapidly increase molecular complexity in as ingle operation. In 2006, Cho and co-workers reported that 3-bromo-5vinyl-2-pyrones underwent tandem Diels-Alderr eactions with allyl vinyl etherst op repare variousn ovel tetracyclic lactones.…”
Section: Iedda Reactions Of 3-bromo-2-pyronesmentioning
confidence: 99%
“…Primary investigations on thermal IEDDA reactions of 3‐bromo‐2‐pyrone with electron‐rich dienophiles were carried out by Posner and co‐workers in 1991. Through reaction of 3‐bromo‐2‐pyrone 125 a with 2,2‐dimethyl‐1,3‐dioxole 132 a and 1,1‐dimethoxyethylene 13 a under thermal conditions, lactone 133 was obtained with good endo ‐selectivity, whereas lactone 134 was achieved with excellent regioselectivity, as shown in Scheme 30 [41] …”
Section: Noncatalytic Iedda Reactionsmentioning
confidence: 99%
“…Without a Lewis acid, DA cycloaddition between compound 2 and MVK required 1 d in toluene at 80°C for completion and gave a 73 % yield of 21 exclusively in the form of the endo product (Entry 12). [18] Although the thermal DA cycloaddition of 2 is less efficient than the Lewis-acid-promoted DA cyclizations, the silyl enol ether moiety in 21 could provide a useful handle for the development of cascade cyclization reactions.…”
Section: Lewis-acid-promoted Da Cycloadditions Of 5-(tertbutyldimethymentioning
confidence: 99%