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Stereochemistry of Congested Cyclophanes Containing Chiral Spirobiindanol Phosphonates: Syntheses, X‐Ray Structure, HPLC Enantioresolution and Clathration Properties
Author(s) -
Consiglio Giuseppe A.,
Finocchiaro Paolo,
Failla Salvatore,
Hardcastle Kenneth I.,
Ross Candace,
Caccamese Salvatore,
Giudice Giuseppe
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199911)1999:11<2799::aid-ejoc2799>3.0.co;2-#
Subject(s) - chemistry , cyclophane , high performance liquid chromatography , stereochemistry , enantiomer , crystallography , organic chemistry , chromatography , crystal structure
The synthesis as well as the stereochemical characterization (in solution) of sterically congested cyclophanes containing the chiral spirobiindanol phosphonate moiety is reported. The Williamson's synthetic procedure used for the preparation of our compounds proved to be very satisfactory and all cyclophanes were obtained in high yield (≥ 70%). Only the [1+1] cyclization products were found to be significatively formed in the reaction.