148555-74-2

Upstream product

• 75-11-6 diiodomethane 
• 129423-29-6 [(1E)-3-phenylprop-1-en-1-yl]boronic acid 
• 1462-75-5 3-phenylpropylmagnesium bromide 
• 109-94-4 formic acid ethyl ester 
• 19261-37-1 2-chloro-3-phenyl-propionaldehyde 
• 31729-70-1 bis(iodozinc)methane 
• 122-97-4 3-Phenyl-1-propanol 
• 129423-31-0 trans-2-benzylcyclopropanol 

Downstream Products

• 136068-12-7 5-oxo-3-benzyl-5-phenylpentanal 
• 129423-31-0 (1S,2S)-2-Benzyl-cyclopropanol 

Relevant academic research and scientific papers

Synthesis of 3,5-Disubstituted 1,2-Dioxolanes through the Use of Acetoxy Peroxyacetals

The synthesis of acetoxyendoperoxyacetal derivatives allowed the formation of functionalized 3,5-disubstituted 1,2-dioxolanes through the formation of reactive peroxycarbenium species under Lewis acid mediation. The introduction of a neutral nucleophile s

Access to Functionalized 3,5-Disubstituted 1,2-Dioxolanes under Mild Conditions through Indium(III) Chloride/Trimethylsilyl Chloride or Scandium(III) Triflate Catalysis

Herein we report the use of catalytic amount of scandium(III) triflate or indium(III) chloride (with trimethylsilyl chloride) for the functionalization of endoperoxyacetals through Sakurai or Mukaiyama reactions. These catalysts allow milder and more practical conditions than those previously reported with improvements in scope and reproducibility. This method allows a full catalytic sequence from cyclopropanols to produce desired functionalized 1,2-dioxolanes. (Figure presented.).

Electrophilic Zinc Homoenolates: Synthesis of Cyclopropylamines from Cyclopropanols and Amines

Metal homoenolates, produced via C-C bond cleavage of cyclopropanols, have been extensively investigated as nucleophiles for the synthesis of β-substituted carbonyl derivatives. Herein, we demonstrate that zinc homoenolates can react as carbonyl-electrophiles in the presence of nucleophilic amines to yield highly valuable trans-cyclopropylamines in good yields and high diastereoselectivities. GSK2879552, a lysine demethylase 1 inhibitor currently in clinical trials for the treatment of small cell lung carcinoma, was synthesized using this strategy.

Diasteroselective preparation of cyclopropanols using methylene bis(iodozinc)

Chemical equations presented. A diastereoselective synthesis of trans-2-substituted cyclopropanols is outlined. Bimetallic CH 2(ZnI)2 was found to react with α-chloroaldehydes to give cyclopropanols in yields of 64-89% and dr's ≥ 10:

Asymmetric Cyclopropanation of 1-Alkenylboronic Esters and Its Application to the Synthesis of Optically Active Cyclopropanols

The first asymmetric cyclopropanation of 1-alkenylboronic esters was realized by diastereofacial selective Simmons-Smith reaction of the esters modified by enantiomerically pure diols such as tetramethyltartaramide.Subsequent oxidation of the resulting cyclopropylboronates gave optically active 2-substituted cyclopropanols in 73-94percent ee.These reactive compounds possess high synthetic potential.