@article{pittir16080, volume = {9}, number = {10}, month = {May}, author = {Hanbin Liu and Kai Deng and Theodore Cohen and Kenneth D Jordan}, title = {Computational study of the stereochemistry of intramolecular carbolithiation of an alkene by a secondary alkyllithium: stereochemistry change caused by a single THF molecule of solvation.}, journal = {Org Lett}, pages = {1911 -- 1914}, year = {2007}, url = {http://d-scholarship-dev.library.pitt.edu/16080/}, abstract = {Theoretical calculations reveal that the 40:1 ratio of trans- to cis-2-methylcyclopentylmethyllithium formed in the cyclization of 6-lithio-1-heptene by intramolecular carbolithiation is due to steric crowding in the transition state for the cis-cyclization pathway when a single THF molecule complexes the lithium cation. In the absence of this specific solvation, the cis-cyclization pathway is predicted to be slightly favored.} }