119039-10-0Relevant articles and documents
An Anionic 3 + 2 Cyclization-Elimination Route to Cyclopentenes
Beak, Peter,Burg, Duglas A.
, p. 1647 - 1654 (2007/10/02)
The formation and reactions of lithium (10) are reported.When 10 is allowed to react with olefins bearing an electron-withdrawing group the 4-substituted cyclopent-1-enecarboxamides 11-19 are produced in 22-89percent yields.Methyl-substituted analogues of 10, the allyllithium reagents 23 and 25, react in a similar manner to produce cyclopentenes that have methyl groups in the 2 or 5 positions.The corresponding lithium and lithium reagents also react with electron-deficient olefins to produce the substituted cyclopentenes 28 and 30, which can be hydrolyzed readily to the carboxylic acid 42.The formation of the cyclopentenes occurs in a stepwise fashion by an initial highly regioselective addition to the electron-deficient olefin by the allyllithium reagent followed by a 5-Endo-Trig cyclization and elimination of benzenesulfinate.The allyllithium 10 undergoes polydeuteration on reaction with methanol-O-d and acetone-d6, alkylation with methyl iodide, and addition-dehydratation on reaction with benzaldehyde.
