First diastereoselective asymmetric carbometallation of chiral vinyl metals

Brasseur, Denis; Rezaei, Hadi; Fuxa, Alain; Alexakis, Alexandre; Mangeney, Pierre; Marek, Ilan; Normant, Jean F.

doi:10.1016/s0040-4039(98)00942-3

Cited by 16 publications

(3 citation statements)

References 9 publications

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“…Zinc(II)−Ar interactions have been largely involved 13c, in organozinc chemistry and can be invoked to explain the diastereoselectivity of the carbocyclization reaction. An interaction between the aromatic moiety and the zinc salt chelated by the carbomethoxy and the nitrogen moieties would lead to diastereomeric transition states 23 and 24 (Figure ).…”

Section: Resultsmentioning

confidence: 99%

Diastereocontrolled Synthesis of Enantioenriched 3,4-Disubstituted β-Prolines

2006

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Section: Resultsmentioning

confidence: 99%

Diastereocontrolled Synthesis of Enantioenriched 3,4-Disubstituted β-Prolines

2006

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“…open transition state could be a p-stacking-type 48 interaction between the electron-poor aromatic ring and the electron-rich allenyl moiety. A p-zinc interaction as reported in the solid state in the case of zinc thiolate species 49 and for explaining the diastereoselectivity of zinc enolate carbocyclizations, 50 allylzincations of vinylmetals 51 or cyclopropanation reactions 52 could also been envisioned.…”

Section: Scheme 17 Scrambling Experimentsmentioning

confidence: 97%

Highly Diastereoselective Syntheses of Propargylic Acid and Homopropargylic Systems

Ferreira¹,

Denichoux²,

Chemla³

et al. 2004

Synlett

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The results of our research dealing with the stereoselective synthesis of propargylic and homopropargylic systems are summarized. In a first part, the stereoselective formation of syn-or anti-disubstituted homopropargylic alcohols from acetylenic oxiranes through S N 2 or double S N 2¢ has been developed. Thus, the two diastereomers of a given homopropargylic alcohol are stereospecifically available. The great impact of Lewis acid activation on the regioselectivity of the ring-opening reactions of propargylic oxiranes is also detailed. In a second part, the preparation and uses of new acetylenic/allenic carbenoids are overviewed; their reactivity towards carbonyl compounds and imines is examined, leading to the highly stereoselective synthesis of acetylenic chlorohydrins, oxiranes and aziridines.

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“…When a metallated allyl ethyl ether is transmetallated to the allylzinc derivative 212, and this is in turn added to the g-alkoxyvinyllithium 213, in the presence of Scheme 7-124 Derivatization of (Z)-b-iodoacrolein to a C 2 -symmetric amine followed by enantioselective allylmetallation [151]. excess magnesium bromide, carbometallation occurs diastereoselectively, and is succeeded by an elimination reaction to give the trans-2-vinyl-substituted secondary cyclopropylcarbinols 214 having three well-defined stereocenters with syn-configuration (Scheme 7-127) [154].…”

Section: 182mentioning

confidence: 99%