Abstract
The ability to affect asymmetric reduction of heterocyclic β-aminoacrylates 1 (n = 1–3) has been assessed with pyrrolidine and piperidone variants generating the corresponding N-heterocyclic β2-amino acids 3b and 5b with high enantioselectivity (≥97% ee) using a Rh/WALPHOS catalyst combination. The use of the carboxylic acid substrate was essential; the corresponding esters do undergo reduction but led to racemic products. The seven-ring azepanone variant (as the carboxylic acid 9b) underwent reduction, but only a minimal level of asymmetric induction was observed.
Original language | English |
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Pages (from-to) | 4124–4127 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 18 |
Issue number | 16 |
Early online date | 10 Aug 2016 |
DOIs | |
Publication status | Published - 19 Aug 2016 |
Keywords
- Asymmetric reduction