Competing domino processes: path-discriminating ability of epoxide stereochemistry at the angular position.
Structurally different products can be reached selectively from unsaturated vicinal bicyclic diols, which differ only by the epoxide configuration at the angular position. It is possible to modify the regiochemical outcome of the domino process in such a way as to create a different pathway, [4 + 2] versus [4 + 3 + 2], and control product distribution by using the configuration bias. No previous example of a domino variant of the [4 + 3 + 2] process appears to have been documented.
Aquino
Maurizio
M
Institut de Chimie des Substances Naturelles, CNRS, F-91198 Gif-sur-Yvette, France.
Safir
Imad
I
Elkhayat
Zobida
Z
Gandara
Zoila
Z
Perez
Manuel
M
Retailleau
Pascal
P
Arseniyadis
Siméon
S
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D004852:Epoxy Compounds / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; D004852:Epoxy Compounds