Syntheses a l'aide de sulfones v(+)- methode de synthese generale de doubles liaisons.

Julia, M.; Paris, Jean‐Marc

doi:10.1016/s0040-4039(01)87348-2

Cited by 602 publications

(213 citation statements)

References 15 publications

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“…The methyl ester 13, which was a mixture of endo and exo isomers, was reduced with lithium borohydride to give the corresponding alcohol 14. Acetylation of 14 with acetyl chloride followed by a Julia elimination 14 With efficient and complementary methods for the production of the azabicyclo[3.3.0]octane 3 in hand, we turned our attention to introduction of the ring functionality necessary to produce a synthetic equivalent to general structure 2, and cyclization of 2 to afford the desired target azanoradamantane 1. The allylic amination described by Sharpless 18 and also by Kresze 19 utilizing bis(p-toluenesulfonyl)sulfur diimide 18 20 is a powerful method of introducing allylic amine functionality via a tandem ene/2,3-sigmatropic rearrangement sequence.…”

Section: Resultsmentioning

confidence: 99%

Synthetic strategies for the construction of enantiomeric azanoradamantanes

Becker¹,

Nosal²,

Zabrowski³

et al. 1997

Tetrahedron

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Section: Resultsmentioning

confidence: 99%

Synthetic strategies for the construction of enantiomeric azanoradamantanes

Becker¹,

Nosal²,

Zabrowski³

et al. 1997

Tetrahedron

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“…1). Among numerous known methods for the syntheses of alkenes including conjugated dienes and oligoenes (12,13), carbonyl olefination reactions, notably Wittig olefination (14) and its variants, such as Horner-Wadsworth-Emmons (HWE hereafter) (15,16), and Still-Gennari (SG hereafter) (17) as well as Ando (18) modifications have been widely used along with related Si-promoted (Peterson) (19) and S-promoted (Julia and Paris) (20) olefination reactions. As useful as these reactions are, they often lack very high (≥98%) stereoselectivity.…”

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confidence: 99%

Highly selective synthesis of conjugated dienoic and trienoic esters via alkyne elementometalation–Pd-catalyzed cross-coupling

Wang

Mohan

Negishi

2011

Proc. Natl. Acad. Sci. U.S.A.

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All four stereoisomers (7-10) of ethyl undeca-2,4-dienoate were prepared in ≥98% isomeric purity by Pd-catalyzed alkenylation (Negishi coupling) using ethyl (E)-and (Z)-β-bromoacrylates. Although the stereoisomeric purity of the 2Z,4E-isomer (8) prepared by Suzuki coupling using conventional alkoxide and carbonate bases was ≤95%, as reported earlier, the use of CsF or n Bu4NF as a promoter base has now been found to give all of 7-10 in ≥98% selectivity. Other widely known methods reveal considerable limitations. Heck alkenylation was satisfactory for the syntheses of the 2E,4E and 2E,4Z isomers of ≥98% purity, but the purity of the 2Z,4E isomer was ≤95%. Mutually complementary HornerWadsworth-Emmons and Still-Gennari (SG) olefinations are also of considerably limited scopes. Neither 2E,4Z nor 2Z,4Z isomer is readily prepared in ≥90% selectivity. In addition to (2Z,4E)-dienoic esters, some (2Z,4E,6E)-and (2Z,4E,6Z)-trienoic esters have been prepared in ≥98% selectivity by a newly devised Pd-catalyzed alkenylation-SG olefination tandem process. As models for conjugated higher oligoenoic esters, all eight stereoisomers for ethyl trideca-2,4,6-trienoate (23-30) have been prepared in ≥98% overall selectivity.highly selective synthesis | Pd-catalyzed Negishi coupling A lkenes represent a large number of natural products of bioactive and medicinally important compounds. Of interest in this study are those containing conjugated dienes and oligoenes (1-11) (Fig. 1). Among numerous known methods for the syntheses of alkenes including conjugated dienes and oligoenes (12, 13), carbonyl olefination reactions, notably Wittig olefination (14) and its variants, such as Horner-Wadsworth-Emmons (HWE hereafter) (15, 16), and Still-Gennari (SG hereafter) (17) as well as Ando (18) modifications have been widely used along with related Si-promoted (Peterson) (19) and S-promoted (Julia and Paris) (20) olefination reactions. As useful as these reactions are, they often lack very high (≥98%) stereoselectivity.In search for highly (≥98%) stereoselective alkene synthesis methodology, our attention was initially drawn to alkyne hydroboration, which generally proceeds in >99% syn-selectivity. Following some promising leads of Brown (21) and Zweifel and co-workers (22-25), we reported in 1973 a couple of highly selective routes to 1,4-disubstituted (E,E)-and (E,Z)-1,3-dienes (1, 3, 26), which appear to represent the earliest syntheses of unsymmetrically substituted conjugated dienes in very high (≥97%) selectivity via organometallic alkenylation.Despite highly selective and satisfactory results described above, our continued search for a more generally applicable and straightforward route to conjugated di-and oligoenes led to the discovery in 1976 of the Pd-catalyzed alkenyl-alkenyl coupling with alkenylalanes (27) and subsequently with alkenyl derivatives containing Zr (28) and Zn (29), collectively known as Negishi coupling (30,31). Along with the subsequently developed alkenylboron version (Suzuki coupling) (32-34), the Pd-catalyzed alken...

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“…In order to move towards the target molecule, component A 2 and B 3 was coupled using Julia olefination 17 . In this regard model experiment was devised to get clues about the conditions and outcome.…”

Section: Scheme 3 Schemementioning

confidence: 99%

Advances in Total Synthesis of Alternaric Acid: An Anti-Fungal and Phytotoxic Natural Product

Ahmad

Yousaf

Zahoor

et al. 2017

J. Chil. Chem. Soc.

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ABSTRACT:Alternaric acid is characterized as 1,4-diene, possessing (E)-1,2-disubstituted alkene known for nanomolar phytotoxic and antifungal activities. This article highlights the major synthetic approaches attempted towards the total synthesis of alternaric acid reported by three groups (Ichihara & coworkers, Trost & coworkers and Johnson and Slade) which involved novel pathways for the rapid construction of this functionalized natural molecule.

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Syntheses a l'aide de sulfones v(+)- methode de synthese generale de doubles liaisons.

Cited by 602 publications

References 15 publications

Synthetic strategies for the construction of enantiomeric azanoradamantanes

Synthetic strategies for the construction of enantiomeric azanoradamantanes

Highly selective synthesis of conjugated dienoic and trienoic esters via alkyne elementometalation–Pd-catalyzed cross-coupling

Advances in Total Synthesis of Alternaric Acid: An Anti-Fungal and Phytotoxic Natural Product

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