ChemInform Abstract: A NEW APPROACH TO THE TOTAL SYNTHESIS OF (.+‐.)‐DEOXYNUPHARIDINE‐ STEREOSPECIFIC REDUCTION OF QUINOLIZINIUM SALTS

Szychowski, J.; Leniewski, Andrzej; Wróbel, Jerzy T.

doi:10.1002/chin.197831351

Chemischer Informationsdienst

1978

DOI: 10.1002/chin.197831351

|View full text |Cite

ChemInform Abstract: A NEW APPROACH TO THE TOTAL SYNTHESIS OF (.+‐.)‐DEOXYNUPHARIDINE‐ STEREOSPECIFIC REDUCTION OF QUINOLIZINIUM SALTS

J. Szychowski¹,

Andrzej Leniewski²,

Jerzy T. Wróbel³

Abstract: Auf dem beschriebenen Weg können in befriedigenden Ausbeuten die Nuphar‐Alkaloide (VIIIa) und (VIIIb) erhalten werden.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2007

2009

Publication Types

Select...

Article2

Relationship

Self Cite0

Independent2

Authors

Journals

Cited by 2 publications

(2 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…5 The relative and absolute stereochemistry of the products was assigned by analogy to 3d , which was bromocyclized to provide single crystals of the corresponding pyridinium cation suitable for X-ray diffraction (Scheme 2). 6 …”

mentioning

confidence: 99%

Palladium-Catalyzed Regio-, Diastereo-, and Enantioselective Benzylic Allylation of 2-Substituted Pyridines

2009

View full text Add to dashboard Cite

We report a new method for the highly regio-, diastereo-, and enantioselective palladium-catalyzed allylic alkylation of 2-substituted pyridines that allows for the formation of homoallylic stereocenters containing alkyl, aryl, heteroaryl, and nitrogen substituents. When the reaction is conducted with asymmetric acyclic electrophiles, both linear and branched products may be obtained exclusively by selecting the appropriate regioisomeric starting material and ligand, an example of the “memory effect.” Deuterium-labeling studies reveal that though no such phenomenon occurs with racemic cyclic electrophiles, the chiral ligand employed reacts kinetically faster with the enantiomer of substrate for which it is “matched,” and yet eventually converts all “mismatched” substrate to product.

show abstract

mentioning

confidence: 99%

Palladium-Catalyzed Regio-, Diastereo-, and Enantioselective Benzylic Allylation of 2-Substituted Pyridines

2009

View full text Add to dashboard Cite

show abstract

“…In order to determine the relative configuration of the product, compound 2g was treated under conditions for bromocyclization ).…”

mentioning

confidence: 99%

Regio- and Diastereoselective Decarboxylative Coupling of Heteroaromatic Alkanes

2007

View full text Add to dashboard Cite

Allylic esters of heteroaromatic alkanes undergo facile palladium-catalyzed decarboxylative coupling. The resulting C−C bond is formed with high diastereoselectivity and high regioselectivity for coupling at the more substituted allyl terminus. It is proposed that this unusual combination of selectivities results from a tandem allylation/aza-Cope rearrangement sequence. After allylation, decarboxylative dearomatization produces an intermediate for the aza-Cope rearrangement. The subsequent aza-Cope rearrangement occurs under mild conditions because it is driven by rearomatization.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

hi@scite.ai

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

ChemInform Abstract: A NEW APPROACH TO THE TOTAL SYNTHESIS OF (.+‐.)‐DEOXYNUPHARIDINE‐ STEREOSPECIFIC REDUCTION OF QUINOLIZINIUM SALTS

Abstract: Auf dem beschriebenen Weg können in befriedigenden Ausbeuten die Nuphar‐Alkaloide (VIIIa) und (VIIIb) erhalten werden.

Cited by 2 publications

References 0 publications

Palladium-Catalyzed Regio-, Diastereo-, and Enantioselective Benzylic Allylation of 2-Substituted Pyridines

Palladium-Catalyzed Regio-, Diastereo-, and Enantioselective Benzylic Allylation of 2-Substituted Pyridines

Regio- and Diastereoselective Decarboxylative Coupling of Heteroaromatic Alkanes

Contact Info

Product

Resources

About