625389-74-4

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 625389-71-1 (+)-(1R,2S)-(2-hydroxymethyl-1-phenyl-cyclopropyl)-methanol 
• 96847-52-8 (1R,2S)-2-oxo-1-phenyl-3-oxabicyclo[3.1.0]hexane 
• 625389-72-2 (1S,2R)-1-(tert-butyldiphenylsiloxy)methyl-2-(N-methoxy-N-methylcarbamoyl)-2-phenylcyclopropane 
• 625389-73-3 (2R,1S)-1-(tert-butyl(diphenyl)silyloxy)methyl-2-hydroxymethyl-2-phenylcyclopropane 

Downstream Products

• 625389-73-3 (2R,1S)-1-(tert-butyl(diphenyl)silyloxy)methyl-2-hydroxymethyl-2-phenylcyclopropane 
• 29667-46-7 (1S,2R)-2-phenylcyclopropylmethanol 
• 110659-58-0 (1S,2S)-trans-1-(hydroxymethyl)-2-phenylcyclopropane 
• 625389-75-5 (1R,2S)-2-((tert-butyldiphenylsilyloxy)methyl)-1-phenylcyclopropanecarboxylic acid 

Relevant academic research and scientific papers

Synthesis of 1-arylpiperazyl-2-phenylcyclopropanes designed as antidopaminergic agents: Cyclopropane-based conformationally restricted analogs of haloperidol

A series of the cyclopropane-based conformationally restricted analogs of haloperidol were designed as potential antidopaminergic agents and were effectively synthesized using highly stereoselective Grignard reaction with tert-butanesulfinyl imines as the key step. Pharmacological evaluation of the compounds showed that the conformational restriction method can effectively work for improving the pharmacological selectivity of a parent compound and also for investigating the bioactive conformation.

The unusual 1,4-chelation-controlled nucleophilic addition to aldehydes with high stereoselectivity. A systematic study of stereoselectivity in the addition reaction of carbon nucleophiles to cis-substituted cyclopropanecarbaldehydes

The addition reaction of carbon nucleophiles to cis-substituted cyclopropanecarbaldehydes was systematically investigated. Ab initio calculations of model cyclopropanecarbaldehydes suggested that the bisected s-cis and s-trans conformers are the only two minimum energy conformers, which are stabilized due to the π-donating stereoelectronic effect of the cyclopropane ring. The experimental results of a series of substrates, that is, cyclopropanecarbaldehydes 1-5 bearing a cis-(tert-butyldiphenylsilyloxy)methyl group, a cis-benzyloxymethyl group, a cis-(p-methoxybenzyloxy)methyl group, cis-N,N-diethylcarbamoyl and trans-phenyl groups, and cis-(tert- butyldiphenylsilyloxy)methyl and trans-phenyl groups, respectively, showed that highly anti-selective Grignard additions could be realized. It turned out that it occurred via an unusual 7-membered 1,4-chelation-controlled pathway. Highly stereoselective Grignard addition via the chelation-controlled pathway occurred even in the reaction of the usually non-chelating silyl ether-type substrate 5. The results have great importance because the 1,4-chelation-controlled stereoselective addition reactions can indeed be realized. Under non-chelation conditions, the syn-products were produced with moderate stereoselectivity, which are likely to be formed via the bisected s-cis conformation-like transition state stabilized by the characteristic orbital interaction. These reactions, especially the chelation-controlled reaction, should be useful because of their t stereoselectivity and stereochemical predictability.

Construction of a cis-Cyclopropane via Reductive Radical Decarboxylation. Enantioselective Synthesis of cis- and trans-1-Arylpiperazyl-2-phenylcyclopropanes Designed as Antidopaminergic Agents

(1S,2S)-, (1S,2R)-, and (1R,2S)-1-(2,4-Dimethylphenyl)piperazyl-2-phenylcyclopropane (2a, 3, and ent-3, respectively), which were designed as conformationally restricted analogues of haloperidol (1), a clinically effective antipsychotic agent, were synthe