Lithiated Carbamates: Chiral Carbenoids for Iterative Homologation of Boranes and Boronic Esters

Stymiest, Jake L.; Dutheuil, Guillaume; Mahmood, Nasir; Aggarwal, Varinder K.

doi:10.1002/anie.200702146

Cited by 237 publications

(82 citation statements)

References 33 publications

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“…Kocienski [14] and Aggarwal [15] showed that the 3-step sequence could be streamlined to a single operation by directly adding a boronic ester to the intermediate chiral organolithium. As outlined in Table 2, a general lithiation-borylation process starts with the asymmetric deprotonation of primary carbamates to give the corresponding enantioenriched organolithiums 12.…”

Section: α-Chloro-stabilized Lithium Carbenoidsmentioning

confidence: 99%

Reagent-Controlled Lithiation–Borylation

Leonori

Aggarwal

2015

Synthesis and Application of Organoboron Compounds

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Section: α-Chloro-stabilized Lithium Carbenoidsmentioning

confidence: 99%

Reagent-Controlled Lithiation–Borylation

Leonori

Aggarwal

2015

Synthesis and Application of Organoboron Compounds

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“…(1)]. [14] Pleasingly,n oc ompeting reactions involving displacement of the vinylic selenide were observed, and allylic boronic ester 3 was obtained in 91 %yield and 99:1 e.r.…”

Section: Allenesareversatilefunctionalgroupsthatcanbeemployedmentioning

confidence: 99%

Enantiodivergent Synthesis of Allenes by Point‐to‐Axial Chirality Transfer

et al. 2018

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General rightsThis document is made available in accordance with publisher policies. Please cite only the published version using the reference above. Full terms of use are available: http://www.bristol.ac.uk/pure/about/ebr-terms Abstract: An enantiodivergent method for the synthesis of multiply substituted allenes is described. Highly enantioenriched,p oint-chiral boronic esters were synthesized by homologation of a-seleno alkenyl boronic esters with lithiated carbamates and eliminated to form axially chiral allene products.B ye mploying either oxidative or alkylative conditions,b oth syn and anti elimination could be achieved with complete stereospecificity.The process enables the synthesis of either Mo rPallenes from as ingle isomer of ap oint-chiral precursor and can be employed for the enantioselective assembly of di-, tri-, and tetrasubstituted allenes.

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“…5 Indeed, reagents comprising organolithium reagents (e.g. s-BuLi or n-BuLi) and (-)-sparteine have been used for the asymmetric synthesis of a diverse range of compounds including amines, 6 alcohols, 7 phosphines, 8 ferrocenes 9 and paracyclophanes. 10 An example from Bailey and Mealy 11,12 is representative of the synthetic potential afforded by organolithium/(-)-sparteine reagents.…”

Section: Introductionmentioning

confidence: 99%