Investigation of Electrostatic Interactions towards Controlling Silylation‐Based Kinetic Resolutions

Zhang, Tian; Redden, Brandon K.; Wiskur, Sheryl L.

doi:10.1002/ejoc.201900754

Cited by 5 publications

(1 citation statement)

References 46 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Subsequently, we examined the reaction using racemic cis ‐ 13 , instead of trans ‐ 13 to investigate the effect of the relative stereochemistry of the substrate under the optimized reaction conditions (Scheme 3, (1)). No reaction occurred, which was in accordance to that previously reported [7c,g] . However, this result indicates that the reaction can be performed with good chemoselectivity using a mixture of cis and trans diastereomers.…”

Section: Figuresupporting

confidence: 92%

Highly Efficient Silylative Kinetic Resolution of Racemic trans‐2‐Alkyl‐1‐indanols Catalyzed by Chiral Guanidine

2021

View full text Add to dashboard Cite

Chiral guanidine catalyzed silylative kinetic resolution of racemic trans-2-alkyl-1-indanols using Ph 3 SiCl was achieved with high s-values. A variety of substrates bearing alkyl groups at the C-2 position and substituents on the aromatic rings of the indanol moiety were applicable in the reaction achieving good to high selectivity, irrespective of the type of substituent present. In addition to exhibiting high selectivity, the guanidine catalyst was found to be highly active and the reactions could be performed using a catalyst loading of only 0.5 mol %. It was revealed that the relative stereochemistry of the stereogenic centers of the substrates was important and that the reaction using cis-substrates did not proceed at all, whereas the reaction can be selectively carried out using trans-substrates.

show abstract

Section: Figuresupporting

confidence: 92%