7393-43-3Relevant articles and documents
A convenient preparation of (S)-(-)-4-hydroxy-2-methylcyclopent-2-en-1-one and its application as a chiral synthetic equivalent of 2-methylcyclopent-2-en- 1-one in the terpenoid synthesis
Michalak, Karol,Wicha, Jerzy
, p. 5073 - 5081 (2014)
A method for the preparation of (S)-4-hydroxy-2-methylcyclopent-2-en-1-one from 1-(2-furyl)ethanol using modified Piancatelli rearrangement and enzymatic kinetic resolution of the racemate was developed. An application of O-protected derivatives of 4-hydroxy-2-methylcyclopent-2-en-1-one to terpenoid synthesis through tandem conjugate addition of allyl-metal reagents, enolate trapping, and consecutive Mukaiyama-Michael addition was studied. An optically active azulene derivative useful for terpenoid synthesis was efficiently synthesized.
A novel mode of access to polyfunctional organotin compounds and their reactivity in Stille cross-coupling reaction
Lamandé-Langle, Sandrine,Abarbri, Mohamed,Thibonnet, Jér?me,Duchêne, Alain
, p. 2368 - 2374 (2009/09/30)
Mono-, di-, tri- and tetra-functional organotin compounds were easily prepared in a sonicated Barbier reaction using ultrasound technology via coupling reaction of organo halides with tin halides (Bu3SnCl, Bu2SnCl2, BuSnCl
On the use of mixtures of organotin species for catalytic enantioselective ketone allylation - A detective story
Cunningham, Anthony,Mokal-Parekh, Vijaya,Wilson, Claire,Woodward, Simon
, p. 741 - 748 (2007/10/03)
In the presence of enantiopure MTBH2 (monothiobinaphthol, 2-hydroxy-2′mercapto-1,1′-binaphthyl; 0.2 eq.) quantitative allylation of ArC(=O)Me takes place with impure Sn(CH2CH=CH2)4 (prepared from allyl chloride, air-oxidised magnesium and SnCl4) to yield tert-homoallylic alcohols in 85-92% ee. In the same process highly purified, or commercial, Sn(CH2CH=CH2)4 yields material of only 35-50% ee. The origin of these effects is the presence of small amounts of the compounds, EtSn(CH2CH=CH2)3, ClSn(CH2CH=CH2)3 ClSnEt(CH2CH=CH2)2 in the tetraallyltin sample and the presence of traces of water (which inhibits achiral background reactions). All the triallyl and diallyl species enhance the stereoselectivity in the catalytic allylation reaction, the chlorides more so than the ethyl compound. Hydrolysis of ClSnEt(CH2CH=CH2)2 affords crystallographically characterised Sn4(μ3-O)(μ2-Cl)2 Cl2Et4(CH2CH=CH2)4. Reaction of this latter compound with MTBH2 leads to the most potent catalyst.
