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- Title
Asymmetric Henry Reaction of Nitromethane with Substituted Aldehydes Catalyzed by Novel In Situ Generated Chiral Bis(β-Amino Alcohol-Cu(OAc) 2 ·H 2 O Complex.
- Authors
Alammari, Abdullah Saleh; Al-Majid, Abdullah Mohammed; Barakat, Assem; Alshahrani, Saeed; Ali, Mohammad; Islam, Mohammad Shahidul
- Abstract
Novel chiral thiophene-2,5-bis(β-amino alcohol) ligands (L1–L5) were designed and synthesized from thiophene-2,5-dicarbaldehyde (3) with chiral β-amino alcohols (4a–e) in 4 steps with overall 23% yields. An in situ generated L-Cu(OAc)2·H2O catalyst system was found to be highly capable catalyst for the asymmetric Henry reaction of nitromethane (7) with various substituted aromatic aldehydes (6a–m) producing chiral nitroaldols product (8a–m) with excellent enantiomeric purity (up to 94.6% ee) and up to >99% chemical yields. 20 mol% of L4-Cu(OAc)2 catalyst complex in EtOH was effective for the asymmetric Henry transformation in 24 h, at ambient temperature. Ease of ligand synthesis, use of green solvent, base free reaction, mild reaction conditions, high yields and excellent enantioselectivity are all key factors that make this catalytic system robust and highly desirable for the access of versatile building block β-nitro alcohol in practical catalytic usage via asymmetric Henry reaction.
- Subjects
NITROALDOL reactions; NITROMETHANE; AMINO alcohols; ENANTIOMERIC purity; ALDEHYDES; CHEMICAL yield; ALCOHOL; AROMATIC aldehydes
- Publication
Catalysts (2073-4344), 2021, Vol 11, Issue 10, p1208
- ISSN
2073-4344
- Publication type
Article
- DOI
10.3390/catal11101208