Research output: Contribution to journal › Article › peer-review
Aldazines were employed in the Castagnoli-Cushman reaction of homophthalic anhydride for the first time. The reaction proved to be distinctly diastereoselective when conducted at room temperature in acetonitrile, yielding predominantly the kinetic cis -configured adduct as a racemate. Thermodynamically more stable trans -configuration could be attained either via heating the cis -configured product in DMSO or via the action of a base (imidazole) in the course of CDI-promoted esterification or amidation of the carboxylic acid function in the initial adducts. Further manipulation of the remaining N -acylhydrazone moiety in the latter led to N -alkyl- or fully unprotected N -aminolactams.
Original language | English |
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Pages (from-to) | 2076-2086 |
Number of pages | 11 |
Journal | Synthesis (Germany) |
Volume | 50 |
Issue number | 10 |
DOIs | |
State | Published - 17 May 2018 |
ID: 34633436