Skip to main content

Research Repository

Advanced Search

All Outputs (6)

On the mechanism and origin of the stereoselectivity in iodo-deboronation and chloro-deboronation of hindered alkenyl boronate esters using either ICI-NaOMe or ICI-pyridine (2004)
Journal Article
Lightfoot, A., Twiddle, S., & Whiting, A. (2004). On the mechanism and origin of the stereoselectivity in iodo-deboronation and chloro-deboronation of hindered alkenyl boronate esters using either ICI-NaOMe or ICI-pyridine. Tetrahedron Letters, 45(46), 8557-8561

Conversion of hindered alkenyl boronate esters into the corresponding iodoalkene, or alkenyl chloride can be carried out stereoselectively using ICl. In the presence of NaOMe, direct reaction of ICl is favoured yielding the E-iodoalkene, however, the... Read More about On the mechanism and origin of the stereoselectivity in iodo-deboronation and chloro-deboronation of hindered alkenyl boronate esters using either ICI-NaOMe or ICI-pyridine.

Mechanistic studies on the formal aza-Diels-Alder reactions of N-aryl imines: evidence for the non-concertedness under Lewis-acid catalysed conditions (2004)
Journal Article
Hermitage, S., Howard, J., Jay, D., Pritchard, R., Probert, M., & Whiting, A. (2004). Mechanistic studies on the formal aza-Diels-Alder reactions of N-aryl imines: evidence for the non-concertedness under Lewis-acid catalysed conditions. Organic and Biomolecular Chemistry, 2(17), 2451-2460. https://doi.org/10.1039/b407293f

The reaction of a para-methoxyaniline, ethyl glyoxalate-derived imine with a series of dienes has resulted in products, which initially suggest the operation of different modes of aza-Diels-Alder reaction. However, a more likely explanation is that a... Read More about Mechanistic studies on the formal aza-Diels-Alder reactions of N-aryl imines: evidence for the non-concertedness under Lewis-acid catalysed conditions.

Preparation of an advanced phenylglycine-derived intermediate en route to the southern hemisphere tetraene of viridenomycin (2004)
Journal Article
Maw, G., Thirsk, C., Toujas, J., Vaultier, M., & Whiting, A. (2004). Preparation of an advanced phenylglycine-derived intermediate en route to the southern hemisphere tetraene of viridenomycin. Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, 1183-1186

A high-yielding synthesis of a phenylglycine derived (E,Z)-dienylboronate en route to the C16-C23 tetraene of the polyene macrolide viridenomycin is described. Crucial to this synthesis was the development of conditions enabling ready access to synth... Read More about Preparation of an advanced phenylglycine-derived intermediate en route to the southern hemisphere tetraene of viridenomycin.

Unexpected temperature, time and solvent effects in the catalytic asymmetric aza-Diels-Alder reaction of an ethyl glyoxylate-derived N-aryl imine with Danishefsky's diene catalysed by a BINOL-zinc complex (2004)
Journal Article
Guillarme, S., & Whiting, A. (2004). Unexpected temperature, time and solvent effects in the catalytic asymmetric aza-Diels-Alder reaction of an ethyl glyoxylate-derived N-aryl imine with Danishefsky's diene catalysed by a BINOL-zinc complex. Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, 711-713

The catalytic asymmetric aza-Diels-Alder reaction of an ethyl glyoxylate-derived N-aryl imine with Danishefsky's diene using a BINOL-zinc complex provides the corresponding cycloadduct with moderate to high enantioselectivity, depending on the solven... Read More about Unexpected temperature, time and solvent effects in the catalytic asymmetric aza-Diels-Alder reaction of an ethyl glyoxylate-derived N-aryl imine with Danishefsky's diene catalysed by a BINOL-zinc complex.

Lewis acid-catalysed aza-Diels-Alder versus Mannich reactions of N-diethyl phosphoryl imino dienophiles with oxygenated dienes and application of a chiral lewis acid (2004)
Journal Article
Di Bari, L., Guillarme, S., Hermitage, S., Howard, J., Jay, D., Pescitelli, G., …Yufit, D. (2004). Lewis acid-catalysed aza-Diels-Alder versus Mannich reactions of N-diethyl phosphoryl imino dienophiles with oxygenated dienes and application of a chiral lewis acid. Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, 708-710

N-Phosphoryl imines react with oxygenated dienes in the presence of Lewis acids to provide either the formal aza-Diels-Alder adduct, or the acyclic Mannich-type addition product, depending upon the catalyst and work up used, which is in agreement wit... Read More about Lewis acid-catalysed aza-Diels-Alder versus Mannich reactions of N-diethyl phosphoryl imino dienophiles with oxygenated dienes and application of a chiral lewis acid.