99295-89-3Relevant academic research and scientific papers
Mechanistic Studies of Diastereoselective Cyclopropanation via Homochiral Ketals. 1. Dioxolane Structural Effects
Mash, Eugene A.,Hemperly, Susan B.,Nelson, Keith A.,Heidt, Philip C.,Deusen, Shawne Van
, p. 2045 - 2055 (2007/10/02)
Compounds structurally related to 2-cyclohexen-1-one 1,4-di-O-benzyl-L-threitol ketal were prepared and subjected to the Simmons-Smith cyclopropanation.From these experiments a mechanistic model for diastereoselective cyclopropanation of common ring syste
HOMOCHIRAL KETALS IN ORGANIC SYNTHESIS. DIASTEREOSELECTIVE CYCLOPROPANATION OF α,β-UNSATURATED KETALS DERIVED FROM 1,4-Di-O-BENZYL-L-THREITOL
Mash, Eugene A.,Nelson, Keith A.
, p. 679 - 692 (2007/10/02)
2-Cykloalken-1-one 1,4-di-O-benzyl-L-threitol ketals undergo efficient and diastereoselective cyclopropanation when treated with an excess of the Simmons-Smith reagent.For example, 2-cyclohexen-1-one 1,4-di-O-benzyl-L-threitol ketal gave in 90-98percent yield a 9:1 mixture of diastereomeric cyclopropanes as established by 62.9 MHz 13C NMR spectroscopy and by hydrolysis of the mixture to (1R,6S)-bicycloheptan-2-one.Sixteen other examples are presented which demonstrate the generality and predictability of the process for 2-cycloalken-1-one ketals, as well as an unfortunate lack of diastereoselectivity for α,β-unsaturated 1,4-di-O-benzyl-L-threitol acetals.
