Reactifs de grignard vinyliques γ fonctionnels

Duboudin, Jean‐Georges; Jousseaume, B.; Saux, A.

doi:10.1016/s0022-328x(00)91989-2

Cited by 125 publications

(53 citation statements)

References 12 publications

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“…Towards that end, cuprate addition to propargylic alcohol 20 afforded diene 21 as a single olefin isomer, which was then protected to afford known allyl methyl ether 22 . 21 Iododesilylation ( 23 ) followed by selective dihydroxylation and oxidative cleavage of the more electron rich olefin afforded aldehyde 25 . Wittig homologation and reduction of the resulting enoate ( 26 ) yielded allylic alcohol 27 .…”

Section: Resultsmentioning

confidence: 99%

Evolution of an oxidative dearomatization enabled total synthesis of vinigrol

et al. 2014

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The evolution of the synthetic strategy resulting in a total synthesis of vinigrol is presented. Oxidative dearomatization/intramolecular Diels-Alder cycloaddition has served as the successful cornerstone for all of the approaches. Extensive radical cyclization efforts to form the tetracyclic core resulted in interesting and surprising reaction outcomes, none of which could be advanced to vinigrol. These cyclization obstacles were successfully overcome by using Heck instead of radical cyclizations. The total synthesis features a trifluoroethyl ether protecting group being used for the first time in organic synthesis. The logic of its selection and the group’s importance beyond protecting the C8a hydroxyl group is presented along with a discussion of strategies for its removal. Because of the compact tetracyclic cage the route is built around many unusual reaction observations and solutions have emerged. For example, a first of its kind Grob fragmentation reaction featuring a trifluoroethyl leaving group has been uncovered, interesting interrupted selenium dioxide allylic oxidations have been observed as well as intriguing catalyst and counterion dependent directed hydrogenations.

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Section: Resultsmentioning

confidence: 99%

Evolution of an oxidative dearomatization enabled total synthesis of vinigrol

et al. 2014

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“…It should be reminded that 3 can be readily and selectively prepared in higher yield by treating propargyl alcohol with MeMgBr in the presence of a catalytic amount of CuI followed by iodinolysis. [10] …”

Section: Resultsmentioning

confidence: 99%

AlCl₃‐Promoted Facile E‐to‐Z Isomerization Route to (Z)‐2‐Methyl‐1‐buten‐1,4‐ylidene Synthons for Highly Efficient and Selective (Z)‐Isoprenoid Synthesis

Wang

Negishi

2009

Eur J Org Chem

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“…This addition proceeded in an anti fashion to give intermediate 2a . The trend is the same in copper-catalyzed reactions of wide scope [62]. In 2001, Negishi applied copper-catalyzed allylmagnesiation to the total synthesis of ( Z )-γ-bisabolene (Scheme 6) [63].…”

Section: Reviewmentioning

confidence: 99%

Recent advances in transition-metal-catalyzed intermolecular carbomagnesiation and carbozincation

Murakami¹,

Yorimitsu²

2013

Beilstein J. Org. Chem.

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SummaryCarbomagnesiation and carbozincation reactions are efficient and direct routes to prepare complex and stereodefined organomagnesium and organozinc reagents. However, carbon–carbon unsaturated bonds are generally unreactive toward organomagnesium and organozinc reagents. Thus, transition metals were employed to accomplish the carbometalation involving wide varieties of substrates and reagents. Recent advances of transition-metal-catalyzed carbomagnesiation and carbozincation reactions are reviewed in this article. The contents are separated into five sections: carbomagnesiation and carbozincation of (1) alkynes bearing an electron-withdrawing group; (2) alkynes bearing a directing group; (3) strained cyclopropenes; (4) unactivated alkynes or alkenes; and (5) substrates that have two carbon–carbon unsaturated bonds (allenes, dienes, enynes, or diynes).

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Reactifs de grignard vinyliques γ fonctionnels

Cited by 125 publications

References 12 publications

Evolution of an oxidative dearomatization enabled total synthesis of vinigrol

Evolution of an oxidative dearomatization enabled total synthesis of vinigrol

AlCl₃‐Promoted Facile E‐to‐Z Isomerization Route to (Z)‐2‐Methyl‐1‐buten‐1,4‐ylidene Synthons for Highly Efficient and Selective (Z)‐Isoprenoid Synthesis

Recent advances in transition-metal-catalyzed intermolecular carbomagnesiation and carbozincation

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Reactifs de grignard vinyliques γ fonctionnels

Cited by 125 publications

References 12 publications

Evolution of an oxidative dearomatization enabled total synthesis of vinigrol

Evolution of an oxidative dearomatization enabled total synthesis of vinigrol

AlCl3‐Promoted Facile E‐to‐Z Isomerization Route to (Z)‐2‐Methyl‐1‐buten‐1,4‐ylidene Synthons for Highly Efficient and Selective (Z)‐Isoprenoid Synthesis

Recent advances in transition-metal-catalyzed intermolecular carbomagnesiation and carbozincation

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AlCl₃‐Promoted Facile E‐to‐Z Isomerization Route to (Z)‐2‐Methyl‐1‐buten‐1,4‐ylidene Synthons for Highly Efficient and Selective (Z)‐Isoprenoid Synthesis