Research output: Contribution to journal › Article › peer-review
The first example of employing a mixed carboxylic-sulfonic anhydride in reaction with imines is reported. Unlike its well-studied isostere homophthalic anhydride, benzo[c][1,2]oxathiin-3(4H)-one 1,1-dioxide gave no product of a formal [4 + 2] cycloaddition and only followed an alternative reaction pathway toward -lactams, presumably, via a formal [2 + 2] cycloaddition (a Staudinger-type reaction). Optimized reaction conditions involve the use of triethylamine as a base promoter, which also allows isolating the product -lactam benzene sulfonic acids as respective triethylammonium salts by conventional column chromatography. The reaction shows some preference to trans-isomer formation; pure diastereomers can be isolated in some cases.
Original language | English |
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Pages (from-to) | 3989-3998 |
Number of pages | 10 |
Journal | Organic and Biomolecular Chemistry |
Volume | 16 |
Issue number | 21 |
DOIs | |
State | Published - 1 Jan 2018 |
ID: 34637274