Directed Ortho (directed + ortho)

Distribution by Scientific Domains


Selected Abstracts


(,)-Sparteine-Mediated Directed ortho- Metalation of N -Cumyl- N -ethylferrocenecarboxamide.

ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 3 2003
Amines, Esters, Phosphines, Versatile Routes to Functionalized Planar Chiral Ferrocenecarboxamides
Abstract N -Cumyl- N -ethylferrocenecarboxamide 5 provides planar chiral carboxamides 6 in high yield and % ee via (,)-sparteine-mediated directed ortho -metalation. Mild decumylation affords secondary amides 7, which serve as intermediates for a convenient and general route to the venerable Ugi planar chiral ferrocenylamines 13 and as versatile precursors for the preparation of novel chiral ferrocenes 15 and 20. The chiral TMS-ferrocenyl derivative 7c is used to prepare the enantiomeric (S)- 7f, circumventing the lack of availability of (+)-sparteine. [source]


Synthesis of deuterium labelled 2-bromobenzylamine by directed ortho -metalation chemistry

JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, Issue 3 2005
Jens Atzrodt
Abstract Directed ortho -metalation (DoM) strategy has been applied for the development of a short procedure for the regiospecific synthesis of [phenyl - 2H4]-2-bromo-benzylamine 6 starting from commercially available [phenyl - 2H5]-benzoyl chloride 1. A strong isotope effect was observed during the ortho -substitution. Copyright © 2005 John Wiley & Sons, Ltd. [source]


ChemInform Abstract: Combined Directed ortho and Remote Metalation,Suzuki Cross-Coupling Strategies.

CHEMINFORM, Issue 43 2009
Efficient Synthesis of Heteroaryl-Fused Benzopyranones from Biaryl O-Carbamates.
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 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. [source]


Combined Directed ortho and Remote Metalation,Cross-Coupling Strategies.

CHEMINFORM, Issue 45 2004
3-a]carbazole Alkaloid., General Method for Benzo[a]carbazoles, the Synthesis of an Unnamed Indolo[
Abstract For Abstract see ChemInform Abstract in Full Text. [source]


Suppressing the Anionic Fries Rearrangement of Aryl Dialkylcarbamates; the Isolation of a Crystalline ortho -Deprotonated Carbamate

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 4 2008
Felipe García
Abstract In the presence of organolithium bases phenyl dialkylcarbamates have previously been shown to undergo facile rearrangement to yield the corresponding salicylamides. However, heterometallic lithium diethyl(2,2,6,6-tetramethylpiperidido)zincate achieves the clean directed ortho -metallation (DoM) of phenyl dialkylcarbamates, with [C6H4{OC(O)NMe2}{Zn(-TMP)Et}Li]2 having been structurally characterized. DFT studies point to a stepwise deprotonative mechanism in which the zincate reagent exhibits kinetic amido basicity. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008) [source]


(,)-Sparteine-Mediated Directed ortho- Metalation of N -Cumyl- N -ethylferrocenecarboxamide.

ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 3 2003
Amines, Esters, Phosphines, Versatile Routes to Functionalized Planar Chiral Ferrocenecarboxamides
Abstract N -Cumyl- N -ethylferrocenecarboxamide 5 provides planar chiral carboxamides 6 in high yield and % ee via (,)-sparteine-mediated directed ortho -metalation. Mild decumylation affords secondary amides 7, which serve as intermediates for a convenient and general route to the venerable Ugi planar chiral ferrocenylamines 13 and as versatile precursors for the preparation of novel chiral ferrocenes 15 and 20. The chiral TMS-ferrocenyl derivative 7c is used to prepare the enantiomeric (S)- 7f, circumventing the lack of availability of (+)-sparteine. [source]


Synthesis of deuterium labelled 2-bromobenzylamine by directed ortho -metalation chemistry

JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, Issue 3 2005
Jens Atzrodt
Abstract Directed ortho -metalation (DoM) strategy has been applied for the development of a short procedure for the regiospecific synthesis of [phenyl - 2H4]-2-bromo-benzylamine 6 starting from commercially available [phenyl - 2H5]-benzoyl chloride 1. A strong isotope effect was observed during the ortho -substitution. Copyright © 2005 John Wiley & Sons, Ltd. [source]


Synthesis of benzoxazole-[phenyl- 13C6] by directed ortho -metalation chemistry

JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, Issue 1 2004
Volker Derdau
Abstract A new method for the preparation of benzoxazole-[phenyl- 13C6] (1) starting from aniline-[13C6] (4) has been developed involving directed ortho -metalation (DoM) chemistry. The synthesis comprises four steps and an overall yield of 39% was obtained. Copyright © 2003 John Wiley & Sons, Ltd. [source]