Synthesis of <scp>d</scp>- and <scp>l</scp>-Carbocyclic Nucleosides via Rhodium-Catalyzed Asymmetric Hydroacylation as the Key Step

Marcé, Patricia; Dı́az, Yolanda; Matheu, M. Isabel; Castillón, Sergio

doi:10.1021/ol801791g

Cited by 55 publications

(26 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…68 Purine systems can also be rapidly functionalized to produce nucleoside analogs in high ee and good dr as opposed to arduous sequences (panel D). 69 The alkylation of estrone with cyclopentyl electrophiles is known to be problematic 70,71 and a four-step alternative route was developed to access such systems (panel E). Using housane (−)-10 , the same intermediate (after desulfonylation) or chiral analogs can be accessed in short order.…”

Section: Strategic Application Of Stereospecific Strain Releasementioning

confidence: 99%

Strain-Release Heteroatom Functionalization: Development, Scope, and Stereospecificity

et al. 2017

View full text Add to dashboard Cite

Driven by the ever-increasing pace of drug discovery and the need to push the boundaries of unexplored chemical space, medicinal chemists are routinely turning to unusual strained bioisosteres such as bicyclo[1.1.1]pentane, azetidine, and cyclobutane to modify their lead compounds. Too often, however, the difficulty of installing these fragments surpasses the challenges posed even by the construction of the parent drug scaffold. This full account describes the development and application of a general strategy where spring-loaded, strained C–C and C–N bonds react with amines to allow for the “any-stage” installation of small, strained ring systems. In addition to the functionalization of small building blocks and late-stage intermediates, the methodology has been applied to bioconjugation and peptide labeling. For the first time, the stereospecific strain-release “cyclopentylation” of amines, alcohols, thiols, carboxylic acids, and other heteroatoms is introduced. This report describes the development, synthesis, scope of reaction, bioconjugation, and synthetic comparisons of four new chiral “cyclopentylation” reagents.

show abstract

Section: Strategic Application Of Stereospecific Strain Releasementioning

confidence: 99%

Strain-Release Heteroatom Functionalization: Development, Scope, and Stereospecificity

et al. 2017

View full text Add to dashboard Cite

show abstract

“…Triphenylphosphine (526 mg, 2.01 mmol) and carbon tetra-bromide (664 mg, 2.00 mmol) were added to a stirred solution of 2-(( tert -butyldiphenylsilyloxy)methyl)prop-2-en-1-ol 47 (662 mg, 2.03 mmol) in CH 2 Cl 2 (8.0 mL) at 0 °C. The reaction mixture was stirred for 40 min and then concentrated in vacuo.…”

Section: Methodsmentioning

confidence: 99%

Studies toward welwitindolinones: formal syntheses of N-methylwelwitindolinone C isothiocyanate and related natural products

McElroy

Shamszad

et al. 2013

Tetrahedron

View full text Add to dashboard Cite

show abstract

“…The alcohol product was further reacted with tetrabutylammonium fluoride (TBAF) in THF to give (1 S ,3 S )−3‐(hydroxymethyl)cyclopentanol in good yield. Starting from the key intermediate (1 S ,3 S )−3‐(hydroxymethyl)cyclopentanol, carbocyclic‐ddA can be readily synthesized following the literature procedure 43…”

Section: Development and Application Of Yanphos For Rh‐catalyzed Ahfmentioning

confidence: 99%

Chiral Ligands for Rhodium‐Catalyzed Asymmetric Hydroformylation: A Personal Account

Chen

Dong

Zhang

2016

The Chemical Record

View full text Add to dashboard Cite

Asymmetric hydroformylation represents one of the most efficient routes for the preparation of chiral aldehydes from alkenes in the presence of syngas in a perfect atom-economic way. During the past few decades, a variety of chiral ligands have been developed for the asymmetric hydroformylation. However, only a few ligands exhibit good performance in terms of the regio- and enantioselectivities. Additionally, for the chiral ligands developed up to now, only limited substrates were tolerated and no examples have led to the application of the asymmetric hydroformylation reaction on a commercial scale due to several technical challenges. This account provides a brief introduction of the current efficient chiral ligands for asymmetric hydroformylation and the ongoing efforts we have made in this field.

show abstract

Synthesis of d- and l-Carbocyclic Nucleosides via Rhodium-Catalyzed Asymmetric Hydroacylation as the Key Step

Cited by 55 publications

References 35 publications

Strain-Release Heteroatom Functionalization: Development, Scope, and Stereospecificity

Strain-Release Heteroatom Functionalization: Development, Scope, and Stereospecificity

Studies toward welwitindolinones: formal syntheses of N-methylwelwitindolinone C isothiocyanate and related natural products

Chiral Ligands for Rhodium‐Catalyzed Asymmetric Hydroformylation: A Personal Account

Contact Info

Product

Resources

About