Titanium isopropoxide-mediated nucleophilic openings of 2,3-epoxy alcohols. A mild procedure for regioselective ring-opening

Caron, Maurice; Sharpless, K. Barry

doi:10.1021/jo00209a047

Cited by 456 publications

(133 citation statements)

References 0 publications

Supporting

Mentioning

129

Contrasting

Unclassified

Order By: Relevance

“…A solution of imido complex 1 (10 mg, 0.027 mmol) in benzene-d 6 (0.5 mL) was added dropwise to a rapidly stirred solution of substituted styrene oxide (0.055 mmol, 2.0 equiv) and styrene oxide (0.055 mmol, 2.0 equiv) in benzene-d 6 (0.7 mL). The solution turned bright orange over 5 min.…”

Section: Equiv Of Epoxidementioning

confidence: 99%

Synthetic and Mechanistic Studies of Strained Heterocycle Opening Reactions Mediated by Zirconium(IV) Imido Complexes

et al. 2005

View full text Add to dashboard Cite

The reactions of the bis(cyclopentadienyl)(tert-butylimido)zirconium complex (Cp 2 Zr=N-t-Bu) (THF) (1) with epoxides, aziridines, and episulfides were investigated. Heterocycles without accessible β-hydrogens undergo insertion/protonation of the C-X bond to produce 1,2-amino alcohols (X = O) and 1,2-diamines (X = NR), whereas heterocycles with accessible β-hydrogens undergo elimination/protonation to produce allylic alcohols (X = O) and allylic sulfides (X = S). Mechanistic investigations support a stepwise pathway with zwitterionic intermediates for the first reaction class and a concerted pathway for the second reaction class. Additionally, the feasibility of chirality transfer from the planar-chiral ebthi (ebthi = ethylenebis(tetrahydroindenyl)) ligand was demonstrated with a chiral analogue, (ebthi)-Zr=NAr(THF) (Ar = 2,6-dimethylphenyl), 2, through the diastereoselective ring opening of meso epoxides.

show abstract

Section: Equiv Of Epoxidementioning

confidence: 99%

Synthetic and Mechanistic Studies of Strained Heterocycle Opening Reactions Mediated by Zirconium(IV) Imido Complexes

et al. 2005

View full text Add to dashboard Cite

show abstract

“…The classical protocol [18] for the ring opening of epoxides by azides described by Caron and Sharpless uses MeOH/H 2 O (8:1) as solvent medium, 5 equiv. of NaN 3 , and 2.2 equiv.…”

Section: Resultsmentioning

confidence: 99%

Regioselectivity Control of the Ring Opening of Epoxides With Sodium Azide in a Microreactor

et al. 2012

View full text Add to dashboard Cite

The reaction of different types of aromatic and aliphatic epoxides with sodium azide to give vicinal azido alcohols was studied in a microreactor with and without pillars in the channels. Dependent on the substrate, the regioselectivity of the ring opening is affected by the used solvent system, viz. acetonitrile-water (sometimes with 10% acetic acid to promote the reactivity of substrates) or t-butyl acetate-water containing Tween80 as a surfactant. For styrene oxide and α-methylstyrene oxide, the α/β regioselectivity changes from 4 to 10 and 1.7 to 6.2, respectively, going from acetonitrile-water to Tween80-containing t-butyl acetate-water. The addition of a surfactant (Tween80) stabilizes the interface in the biphasic t-butyl acetate-water. Pillar-containing microreactors gave better conversions than microreactors without pillars and lab scale reactions, probably due to better mixing.

show abstract

“…Thioessigsäure allein oder kombiniert mit Na 2 CO 3 setzte das Vinylepoxid 4 nur unvollständig um, während Cs 2 CO 3 , Triethylamin, Hünig-Base oder Pyridin als Zusätze 4 zersetzten. Thioessigsäure bewirkte zwar in Gegenwart von Ti(OiPr) 4 eine Ringöffnung von 2,3-Epoxy-1-hexanol, [30] aber keine von 4. Wir konnten jedoch Mischungen aus 4 und Thioessigsäure mit anderen Lewis-Säuren aktivieren (siehe Tabelle 1).…”

unclassified

Variationsfähige Synthese der optisch aktiven Thiotetronsäure‐Antibiotika Thiolactomycin, Thiotetromycin und 834‐B1

Dormann

Brückner

2007

Angewandte Chemie

View full text Add to dashboard Cite

Titanium isopropoxide-mediated nucleophilic openings of 2,3-epoxy alcohols. A mild procedure for regioselective ring-opening

Cited by 456 publications

References 0 publications

Synthetic and Mechanistic Studies of Strained Heterocycle Opening Reactions Mediated by Zirconium(IV) Imido Complexes

Synthetic and Mechanistic Studies of Strained Heterocycle Opening Reactions Mediated by Zirconium(IV) Imido Complexes

Regioselectivity Control of the Ring Opening of Epoxides With Sodium Azide in a Microreactor

Variationsfähige Synthese der optisch aktiven Thiotetronsäure‐Antibiotika Thiolactomycin, Thiotetromycin und 834‐B1

Contact Info

Product

Resources

About