Abstract
Helical chiral 1,12-dimethylbenzo[c]phenanthrene-5,8-dicarboxylic acid was synthesized and resolved in multigram quantities. The absolute configuration was determined by X-ray analysis of the bis(camphorsultamamide) derivative. A series of optically active macrocyclic amides consisting of the chiral unit and a dianiline spacer were synthesized by one-pot procedures, and their structures were compared by spectroscopy and X-ray crystallography. One of the cycloamides exhibited catalytic activity in the asymmetric addition of diethylzinc to aromatic aldehydes. N-Alkylated derivatives were also synthesized, which possessed folded structures distinct from those of the parent cyclic amides.
Original language | English |
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Pages (from-to) | 9500-9509 |
Number of pages | 10 |
Journal | Journal of Organic Chemistry |
Volume | 63 |
Issue number | 25 |
DOIs | |
Publication status | Published - 1998 Dec 11 |
ASJC Scopus subject areas
- Organic Chemistry