2005
DOI: 10.1002/ange.200501686
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Domino Reaction of 2,3‐Epoxy‐1‐alcohols and PIFA in the Presence of H2O and the Concise Synthesis of (+)‐Tanikolide

Abstract: The domino reaction can perform several reactions in a single operation and is a very powerful tool to synthesize organic compounds. The development of new and efficient domino

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Cited by 11 publications
(7 citation statements)
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“…Further oxidization reaction of 2 by PIFA occurs to generate intermediate C, which is attacked by water to give intermediates D and E when aqueous solvent is employed. [30,31] In the presence of PIFA, alcohol E is easily oxidized to give rise to final product 3. [21d,30a,32] …”
Section: Resultsmentioning
confidence: 99%
“…Further oxidization reaction of 2 by PIFA occurs to generate intermediate C, which is attacked by water to give intermediates D and E when aqueous solvent is employed. [30,31] In the presence of PIFA, alcohol E is easily oxidized to give rise to final product 3. [21d,30a,32] …”
Section: Resultsmentioning
confidence: 99%
“…A Baeyer-Villiger oxidation of 8 with m-chloroperbenzoic acid (mCPBA) furnished 9 in 87 % yield. In comparison to existing enantioselective syntheses of (+)-9, [15] our route is concise and affords tanikolide in virtually optically pure form and favorable overall yield. Moreover, this route should be useful for the asymmetric synthesis of analogues of tanikolide.…”
mentioning
confidence: 88%
“…We applied this reaction to the development of a concise enantioselective total synthesis of (+)-tanikolide (9) to explore its synthetic utility. [14,15] Our approach features the conjugate addition of b-ketoester 2 B to 3 a catalyzed by QD-1 c as the asymmetric induction step (see Scheme 3). We performed the conjugate addition at À25 8C with 10 mol % of QD-1 c to achieve optimum enantioselectivity.…”
mentioning
confidence: 99%
“…3-Alkyl-2,3-epoxy-1-alcohols: The results of the reactions of the monocyclic 3-alkyl-2,3-epoxy-1-alcohols, 15, have been reported previously in reference [7]. This reaction proceeded in a different manner (Table 3).…”
Section: Resultsmentioning
confidence: 88%
“…[7] The reactions, especially those in the presence of water, provided a very useful domino reaction for producing lactols. We examined this domino reaction in detail and found that trisubstituted 2-alkyl-2,3-epoxy-1-alcohols gave a different type of lactols, which were converted into the corresponding lactones (Scheme 3).…”
Section: Introductionmentioning
confidence: 99%