Abstract Treatment of N-allyl-N-3-butenyl-N-Cbz-amIne ( 1 ) with thexyl borane followed by cyanid... more Abstract Treatment of N-allyl-N-3-butenyl-N-Cbz-amIne ( 1 ) with thexyl borane followed by cyanidation affords an azacyclononanone 2 in 35% yield which can be transformed into δ-coniceine ( 3 ) by catalytic reduction.
The lack of efficient methods to aminate carbanions (R-Metal to RNH2) limits the strategies for a... more The lack of efficient methods to aminate carbanions (R-Metal to RNH2) limits the strategies for alkaloid synthesis. Among the various electrophilic nitrogen reagents used to effect this transformation, chloramine, hydroxylamine-0-mesitylsulfonate, nitrosyl chloride and tosyl azide are the most popular, each affording useful yields of the desired transformation in selected instances. We reasoned that an ideal electrophilic nitrogen agent should react by addition to an unsaturated nitrogen (à la tosyl azide) rather than by displacement of a leaving group at an electron rich center (chloramine). Further, the carbanion-nitrogen adduct should be relatively stable needing minimal manipulations to the desired amine in contrast with nitrosyl chloride. Diazonium ions and nitroso compounds seemed to have these properties; we report here observations concerning the reactions of Grignards and enolates with phenyldiazonium fluoborate.
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Page 1. 8 J. Org. Chem. 1983, 48, 8-16 Epoxyannulation. 4. Reactions of 1,5-, 1,6-, and 1,7-Oxosu... more Page 1. 8 J. Org. Chem. 1983, 48, 8-16 Epoxyannulation. 4. Reactions of 1,5-, 1,6-, and 1,7-Oxosulfonium Salts Michael E. Garst,* Bill J. McBride, and Alan T. Johnson' Department of Chemistry, Uniuersity of California-S'an Diego ...
Die aus der Säure (Ia) erhaltenen ungesättigten Amide (Ib) bzw. (Ic) werden thermisch zu (II) und... more Die aus der Säure (Ia) erhaltenen ungesättigten Amide (Ib) bzw. (Ic) werden thermisch zu (II) und (III) cyclisiert bzw. acetyliert.
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Abstract Treatment of N-allyl-N-3-butenyl-N-Cbz-amIne ( 1 ) with thexyl borane followed by cyanid... more Abstract Treatment of N-allyl-N-3-butenyl-N-Cbz-amIne ( 1 ) with thexyl borane followed by cyanidation affords an azacyclononanone 2 in 35% yield which can be transformed into δ-coniceine ( 3 ) by catalytic reduction.
The lack of efficient methods to aminate carbanions (R-Metal to RNH2) limits the strategies for a... more The lack of efficient methods to aminate carbanions (R-Metal to RNH2) limits the strategies for alkaloid synthesis. Among the various electrophilic nitrogen reagents used to effect this transformation, chloramine, hydroxylamine-0-mesitylsulfonate, nitrosyl chloride and tosyl azide are the most popular, each affording useful yields of the desired transformation in selected instances. We reasoned that an ideal electrophilic nitrogen agent should react by addition to an unsaturated nitrogen (à la tosyl azide) rather than by displacement of a leaving group at an electron rich center (chloramine). Further, the carbanion-nitrogen adduct should be relatively stable needing minimal manipulations to the desired amine in contrast with nitrosyl chloride. Diazonium ions and nitroso compounds seemed to have these properties; we report here observations concerning the reactions of Grignards and enolates with phenyldiazonium fluoborate.
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Page 1. 8 J. Org. Chem. 1983, 48, 8-16 Epoxyannulation. 4. Reactions of 1,5-, 1,6-, and 1,7-Oxosu... more Page 1. 8 J. Org. Chem. 1983, 48, 8-16 Epoxyannulation. 4. Reactions of 1,5-, 1,6-, and 1,7-Oxosulfonium Salts Michael E. Garst,* Bill J. McBride, and Alan T. Johnson' Department of Chemistry, Uniuersity of California-S'an Diego ...
Die aus der Säure (Ia) erhaltenen ungesättigten Amide (Ib) bzw. (Ic) werden thermisch zu (II) und... more Die aus der Säure (Ia) erhaltenen ungesättigten Amide (Ib) bzw. (Ic) werden thermisch zu (II) und (III) cyclisiert bzw. acetyliert.
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
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