Abstract
The development of robust and efficient strategies to access structurally diverse drug-like compound collections remains an important challenge for small molecule probe development and drug discovery. Following a build/couple/pair strategy we have established bidirectional approach to unprecedented benzoxazepines by employing a Pictet–Spengler/aza-Michael addition cascade and Schiff base/aza-Michael addition/reduction protocols, respectively. The corresponding β-carboline-fused benzoxazepines and peripherally substituted benzoxazepines are isolated in high diastereoselectivity, good to excellent yields and have, to the best of our knowledge, never been reported.
Original language | English (US) |
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Pages (from-to) | 14182-14192 |
Number of pages | 11 |
Journal | Chemistry - A European Journal |
Volume | 23 |
Issue number | 57 |
DOIs | |
State | Published - Oct 12 2017 |
Keywords
- Pictet–Spengler reaction
- aza-Michael addition
- benzoxazepines
- diversity oriented synthesis
- stereoselective synthesis
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry