Synthesis trisubstituted cyclopentene

Nair V, Vellalath S, Poonoth M, Suresh E (2006b) N-heterocyclic carbene-cata-lyzed reaction of chalcones and enals via homoenolate an efficient synthesis of 1,3,4-trisubstituted cyclopentenes. J Am Chem Soc 128 8736-8737... 

Movassaghi M, Schmidt MA (2005) N- Ielcrocyclic carbene-catalyzed amida-tion of unactivated esters with amino alcohols. Org Lett 7 2453-2456 Nair V, Vellalath S, Poonoth M, Mohan R, Suresh E (2006a) N- Ielcrocyclic carbene catalyzed reaction of enals and 1,2-dicarbonyl compounds stereoselective synthesis of spiro y-butyrolactones. Org Lett 8 507-509 Nair V, Vellalath S, Poonoth M, Suresh E (2006b) V-Heterocyclic carbene-catalyzed reaction of chalcones and enals via homoenolate an efficient synthesis of 1,3,4-trisubstituted cyclopentenes. J Am Chem Soc 128 8736-8737... 

Later, these authors reported the synthesis of chiral cis-l,3,4-trisubstituted cyclopentenes based on an enantioselective N-heterocyclic carbene-catalyzed domino annulation of a,p-unsaturated aldehydes and 4-oxoenoates [236]. The domino products were achieved in low to high yields (25-93%), in moderate to... 

In 2006, Nair disclosed the synthesis of ( )-tra s-l,3,4-trisubstituted cyclopentenes resulting from the addition of enals to chalcones catalysed by an achiral carbene." " Mechanistically, the addition of the generated homo-enol to enones to give adduct II, followed by intramolecular acylation to afford cyclopentane-fused p-lactone IV. The final cyclopentene 67 was formed by the in situ decarboxylation of the p-lactones (Scheme 20.32). The enantioselective variant of the process to access ds-cyclopentenes was reported by Bode et al. in 2007. ... 

A total synthesis of ( )-allosamizoline from a symmetrical trisubstituted cyclopentene has been reported, and a synthesis of allosamidin and its (1- 3) linked isomer includes a review of the preparation of the starting aminocyclitol and disaccharide moieties. The synthesis of allosamizoline and allosamidin and isomers is also mentioned in Chapters 3 and 18. 

Roberts RA, Schiill V, Paquette LA (1983) Electrophile-initiated Ring-opening Reactions of 2-Methylene-6,6-dimethylbicyclo [3.1.0] hexanes. New Methodology for the Synthesis of Highly Functionalized 1,2,3-Trisubstituted Cyclopentenes. J Org Chem 4 2076... 

A conceptually surprising and new route to prostaglandins was found and evaluated by C.R. Johnson in 1988. It involves the simple idea to add alkenylcopper reagents stereo-selectively to a protected chiral 4,5-dihydroxy-2-cyclopenten-l-one and to complete the synthesis of the trisubstituted cyclopentanone by stereoselective allylation of the resulting enolate. 

---