ArticleOrganic letters2011
Thermodynamic control of 1,3-boratropic shifts of α- and γ-stannyl-substituted allylboranes: hyperconjugation outweighs steric effects.
Article in Organic letters, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- (Chemical science · 2019Article
- Article
- Article
- Enantioselective synthesis of (Z)- and (E)-2-methyl-1,5-anti-pentenediols via an allene hydroboration-double-allylboration reaction sequence.Journal of the American Chemical Society · 2013Article
- Enantioselective synthesis of (E)-δ-silyl-anti-homoallylic alcohols via an enantiodivergent hydroboration-crotylboration reaction of a racemic allenylsilane.Organic letters · 2013Article
- Diastereo- and enantioselective synthesis of (E)-2-Methyl-1,2-syn- and (E)-2-Methyl-1,2-anti-3-pentenediols via allenylboronate kinetic resolution with ((d)Ipc)2BH and aldehyde allylboration.Organic letters · 2012Article
- Enantioselective synthesis of (-)-basiliskamide A.Organic letters · 2012Article
- Highly stereoselective synthesis of anti,anti-dipropionate stereotriads: a solution to the long-standing problem of challenging mismatched double asymmetric crotylboration reactions.Journal of the American Chemical Society · 2012Article
- Enantioconvergent hydroboration of a racemic allene: enantioselective synthesis of (E)-δ-stannyl-anti-homoallylic alcohols via aldehyde crotylboration.Journal of the American Chemical Society · 2011Article
- Enantioselective syntheses of syn- and anti-β-hydroxyallylsilanes via allene hydroboration-aldehyde allylboration reactions.Organic letters · 2011Article
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Authors and funding
4 authors.
Funding
Abstract
(E)-δ-Stannyl homoallylic alcohols are prepared by an allene hydroboration-aldehyde allylboration sequence ( Chen , M. et al. J. Am. Chem. Soc. 2010 , 132, 7881 ). Key to this reaction sequence is that the kinetic allene hydroboration product, 2a, is less stable than and isomerizes to the more sterically congested α-stannylallylborane 3a (see abstract figure). An M06-2X density functional analysis shows that the C-Sn to boron σ-π hyperconjugation interaction is sufficiently stabilizing to override the steric congestion in 3a.
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