Mild metal-free syn-stereoselective ring opening of activated epoxides and aziridines with aryl borates

Chemical Communications

Volumn , Issue 11, 2005, Pages 1426-1428

  Pineschi, Mauro ^a   Bertolini, Ferruccio ^a   Haak, Robert M ^a   Crotti, Paolo ^a   Macchia, Franco ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBON; AZIRIDINE DERIVATIVE; BORIC ACID; CATECHOL; EPOXIDE; INDANONE DERIVATIVE; LEWIS ACID; PALLADIUM; PHENOL DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE;

EID: 16444370558     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b416517a     Document Type: Article

References (20)

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11. 3 with a phenol followed by evaporation of the volatiles under a vacuum.
12. 2 (30 mL) and washed with brine (3.0 ml) for reactions carried out with borate 1b and with 5% NaOH for reactions performed with 1a. Evaporation of the dried organic solution afforded a crude reaction mixture which was subjected to flash chromatography to give the pure compounds 2-12.
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20. The little or no reactivity of trialkyl borates, with vinyl and aryl epoxides respectively, might be ascribed to the fact that the B-OAr bond is reasonably more polarized than the corresponding B-OR bond, due to the greater stabilization of a phenoxide anion with respect to an alkoxide anion.