Abstract
An enantioselective intramolecular [2+2+2] cycloaddition of 2-aminophenol-tethered triynes and diyne-nitriles proceeded using the chiral Rh catalysts, and tripodal cyclophanes and pyridinophanes with a long ansa chain (up to [16]pyridinophane) were obtained in acceptable yield with high to almost perfect ee. In the reaction of triynes, we elucidated that the oxygen atom at the alkyne terminus is essential for the excellent enantioselectivity. For the construction of cage-type molecule, the choice of rigid tether, which connects 1,6-diyne moiety with a side carbon chain having alkyne or cyano group on its terminus, was important, and 8-amino-2-naphthol moiety was also a preferable tether.
Original language | English |
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Pages (from-to) | 2679-2686 |
Number of pages | 8 |
Journal | Tetrahedron |
Volume | 68 |
Issue number | 12 |
DOIs | |
Publication status | Published - 2012 Mar 25 |
Keywords
- Cycloaddition
- Cyclophane
- Enantioselective
- Planar chirality
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry