357426-87-0Relevant academic research and scientific papers
An unexpected reversal of diastereoselectivity in the [4+3]-cycloaddition reaction of nitrogen-stabilized oxyallyl cations with methyl 2-furoate
Antoline, Jennifer E.,Hsung, Richard P.
, p. 739 - 744 (2008/12/23)
An unexpected reversal of diastereoselectivity in the [4+3] cycloaddition of methyl 2-fuorate with nitrogen-stabilized oxyallyl cations derived from epoxidation of chiral allenamides is described here. This intriguing reversal in favor of the endo-II cycloaddition pathway is likely a result of minimizing the dipole interaction between the oxyallyl cation and ester carbonyl of methyl 2-fuorate. Georg Thieme Verlag Stuttgart.
