62894-14-8

Upstream product

• 100-39-0 benzyl bromide 
• 25484-62-2 cis-6-oxabicyclo<3.1.0>cyclohexan-2-ol 
• 68241-89-4 [(cyclopent-2-en-1-yloxy)methyl]benzene 
• 3212-60-0 cyclopent-2-enol 
• 930-30-3 cyclopent-2-enone 

Downstream Products

• 84131-68-0 rac-3-butylcyclopentanone 
• 84131-71-5 3-(Benzyloxy)-2-n-butyl-1-cyclopentanol 
• 84131-69-1 2-(Benzyloxy)-5-n-butyl-1-cyclopentanol 
• 84131-70-4 1,3-Bis(benzyloxy)-2-butylcyclopentane 
• 84131-73-7 3-(Benzyloxy)-5-hydroxycyclopentaneacetonitrile 
• 84131-72-6 3-(Benzyloxy)-2-hydroxycyclopentaneacetonitrile 
• 84131-74-8 2,5-Bis(benzyloxy)cyclopentaneacetonitrile 

Relevant academic research and scientific papers

Diastereoselective epoxidation of allylically substituted alkenes using metalloporphyrin catalysts

Diastereoselective epoxidation of allylically substituted alkenes using metalloporphyrins as catalyst provides high trans-selectivities (i.e., trans-:cis-epoxide ratio). A diversity of cycloalkenes bearing different allylic substituents are shown to be efficiently epoxidized to afford the corresponding trans-epoxides with excellent trans-selectivities (up to >98%) and good yields (up to 99%). Acyclic allylic alkenes bearing different allylic substituents are efficiently epoxidized to afford the corresponding erythro-epoxides with good erythro-selectivities. The metalloporphyrin-catalyzed reactions exhibit up to 20 times higher trans-selectivities than the conventional method using m-chloroperoxybenzoic acid as oxidant.

Highly diastereoselective epoxidation of allyl-substituted cycloalkenes catalyzed by metalloporphyrins

Highly diastereoselective epoxidations of allyl-substituted cycloalkenes including allylic alcohols, esters, and amines using sterically bulky metalloporphyrins [Mn(TDCPP)Cl] (1) and [Ru(TDCPP)CO] (2) as catalysts have been achieved. The "1 + H2O2" and "2 + 2,6-Cl2pyNO" protocols afforded trans-epoxides selectively in good yields (up to 99%) with up to >99:1 trans-selectivity.

Regiochemical Control of the Ring-Opening of Epoxides by Means of Chelating Processes, 13. Synthesis and Ring-Opening Reactions of the Diastereoisomeric cis- and trans-Epoxides Derived from 3-(Benzyloxy)cyclopentene and 2-(Benzyloxy)-2,5-dihydrofuran

The regiochemical outcome of the ring-opening of epoxides bearing remote polar functionalities has been established in the case of carbocyclic (1 and 2) and the corresponding furanosidic (3 and 4) title epoxides. Under standard conditions, the regioisomeric C-1 products are the sole (from trans epoxides 2 and 4) or predominant (from cis epoxides 1 and 3) ring-opening products. However, under chelating conditions, and only in the case of the cis epoxides 1 and 3, a consistent increase in C-2 selectivity is unexpectedly observed. - Keywords: Epoxides; Regioselectivity; Nucleophilic additions; Synthetic methods

Synthetic Approaches to 11-Deoxy-7-oxaprostaglandin Analogues

A synthesis of 11-deoxy-7-oxa prostanoids is presented.The synthesis of this new series of prostaglandin analogues commences with cis-2,3-epoxycyclopentanol (1), protected as an appropriate ether.The key step is the highly regioselective opening of that epoxide with an alkynyl alane reagent.For definition of the scope of that reaction, a brief study of the behavior of other carbon-centered nucleophiles with epoxide 1 was undertaken.It was found that only the alanyl reagent is selective in the desired direction.A rationalization for that selectivity is offered.Following the synthesis herein, over 30 analogues were prepared.Among them are eight optically pure compounds, including four isomers of 11-deoxy-7-oxaprostaglandin E1.