Cyclic Alkenyl Boronic Half Acid Synthesis and Applications

McNulty, LuAnne M.; Kohlbacher, Kris; Borin, Katie; Dodd, Bryan; Bishop, Jeni; Fuller, Lindsey; Wright, Zach

doi:10.1021/jo1003423

Cited by 17 publications

(3 citation statements)

References 22 publications

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“…No syn isomer was detected by 1 H NMR (400 MHz), proving the anti / syn selectivity is >95:5. It is likely that an acyclic homoallylic alcohol having ( Z )-geometry is initially formed and then cyclizes into a six-membered ring structure during workup/purification . The corresponding ( E )-isomer 4aa , remaining in the acyclic form, was observed in ca.…”

Section: Resultsmentioning

confidence: 99%

Enantioselective Synthesis of anti-1,2-Oxaborinan-3-enes from Aldehydes and 1,1-Di(boryl)alk-3-enes Using Ruthenium and Chiral Phosphoric Acid Catalysts

et al. 2017

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A cationic ruthenium(II) complex catalyzes double-bond transposition of 1,1-di(boryl)alk-3-enes to generate in situ 1,1-di(boryl)alk-2-enes, which then undergo chiral phosphoric acid catalyzed allylation of aldehydes producing homoallylic alcohols with a (Z)-vinylboronate moiety. 1,2-Anti stereochemistry is installed in an enantioselective manner. The (Z)-geometry forged in the products allows their isolation in a form of 1,2-oxaborinan-3-enes, upon which further synthetic transformations are operated.

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Section: Resultsmentioning

confidence: 99%

Enantioselective Synthesis of anti-1,2-Oxaborinan-3-enes from Aldehydes and 1,1-Di(boryl)alk-3-enes Using Ruthenium and Chiral Phosphoric Acid Catalysts

et al. 2017

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“…Subsequent reaction with PhCHO followed by basic work-up gave the boracyclic hemiester 10 in 95 % yield and perfect selectivity. This reaction initially gave a mixture of the pinacol boronic ester and the hemiester [16] but addition of NaOH in the workup fully converted the mixture into the hemiester. Suzuki-Miyaura cross-coupling [17] with tolyl iodide gave the tetrasubstituted alkene 11 in > 99:1 d.r.…”

Section: Methodsmentioning

confidence: 99%

Highly Selective Allylborations of Aldehydes Using α,α‐Disubstituted Allylic Pinacol Boronic Esters

et al. 2014

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α,α-Disubstituted allylic pinacol boronic esters undergo highly selective allylborations of aldehydes to give tetrasubstituted homoallylic alcohols with exceptional levels of anti-Z-selectivity (>20:1). The scope of the reaction includes both acyclic and cyclic allylic boronic esters which leads to acyclic and exocyclic tetrasubstituted homoallylic alcohols. The use of β-borylated allylic boronic esters gave fully substituted alkenes bearing a boronic ester which underwent further cross-coupling enabling a highly modular and stereoselective approach to the synthesis of diaryl tetrasubstituted alkenes. Computational analysis revealed the origin of the remarkable selectivity observed.

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“…Although the terminal alkenyl boronates can be prepared by a number of procedures, cross metathesis (CM) of alkenes with vinyl boronates has recently emerged as a new, efficient catalytic method . Taking into account that the introduction of a propenyl moiety on a phenyl ring is easier than the introduction of a propynyl group due to its lower reactivity, we envisaged that the cross-olefin metathesis reaction could be useful for the development of a general protocol to prepare 3-arylpropen-1-yl boronic esters 3 .…”

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confidence: 99%

Synthesis of Alkenyl Boronates from Allyl-Substituted Aromatics Using an Olefin Cross-Metathesis Protocol

2013

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An efficient synthesis of 3-aryl-1-propenyl boronates from pinacol vinyl boronic ester and allyl-substituted aromatics by cross metathesis is reported. Although the allylbenzene derivatives are prone to isomerization reaction under metathesis conditions, we found that some ruthenium catalysts are effective for this methodology. This strategy thus provides an interesting alternative approach to alkyne hydroboration, leading to the preparation of unknown compounds. Moreover, the boron substituent can be replaced by various functional groups in good yields.

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Cyclic Alkenyl Boronic Half Acid Synthesis and Applications

Cited by 17 publications

References 22 publications

Enantioselective Synthesis of anti-1,2-Oxaborinan-3-enes from Aldehydes and 1,1-Di(boryl)alk-3-enes Using Ruthenium and Chiral Phosphoric Acid Catalysts

Enantioselective Synthesis of anti-1,2-Oxaborinan-3-enes from Aldehydes and 1,1-Di(boryl)alk-3-enes Using Ruthenium and Chiral Phosphoric Acid Catalysts

Highly Selective Allylborations of Aldehydes Using α,α‐Disubstituted Allylic Pinacol Boronic Esters

Synthesis of Alkenyl Boronates from Allyl-Substituted Aromatics Using an Olefin Cross-Metathesis Protocol

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