doi: 10.1039/c1ob05966a.
Epub 2011 Sep 20.
Synthesis of 2,3,5,6-tetrahydro-1-alkyl/aryl-1H-benzo[f]chromen-3-ol derivatives from β-tetralones and α,β-unsaturated aldehydes
Affiliations
- PMID: 21931922
- DOI: 10.1039/c1ob05966a
Item in Clipboard
Synthesis of 2,3,5,6-tetrahydro-1-alkyl/aryl-1H-benzo[f]chromen-3-ol derivatives from β-tetralones and α,β-unsaturated aldehydes
Org Biomol Chem.
.
Abstract
Organocatalytic domino Michael-hemiacetalization of β-tetralones with α,β-unsaturated aldehydes is presented. Treatment of β-tetralones with α,β-unsaturated aldehydes in the presence of diphenylprolinol silyl ether gave 2,3,5,6-tetrahydro-1-alkyl/aryl-1H-benzo[f]chromen-3-ol derivatives with high to excellent chemical yields (50-99%) and high levels of enantioselectivities (up to 96% ee).
Similar articles
-
Catalytic enantioselective domino oxa-michael/aldol condensations: asymmetric synthesis of benzopyran derivatives.Chemistry. 2007;13(2):574-81. doi: 10.1002/chem.200600572. Chemistry. 2007. PMID: 17039558
-
Organocatalytic asymmetric tandem Michael addition-hemiacetalization: a route to chiral dihydrocoumarins, chromanes, and 4H-chromenes.J Org Chem. 2010 Oct 15;75(20):6900-7. doi: 10.1021/jo101446d. J Org Chem. 2010. PMID: 20857918
-
Organocatalytic asymmetric Friedel-Crafts alkylation/cyclization cascade reaction of 1-naphthols and alpha,beta-unsaturated aldehydes: an enantioselective synthesis of chromanes and dihydrobenzopyranes.J Org Chem. 2009 Sep 4;74(17):6881-4. doi: 10.1021/jo901409d. J Org Chem. 2009. PMID: 19663397
-
Enantioselective organocatalytic tandem Michael-Aldol reactions: one-pot synthesis of chiral thiochromenes.J Am Chem Soc. 2006 Aug 16;128(32):10354-5. doi: 10.1021/ja063328m. J Am Chem Soc. 2006. PMID: 16895386
-
α-Functionally Substituted α,β-Unsaturated Aldehydes as Fine Chemicals Reagents: Synthesis and Application.Molecules. 2021 Jul 15;26(14):4297. doi: 10.3390/molecules26144297. Molecules. 2021. PMID: 34299572 Free PMC article. Review.
Cited by
-
Recent Advances in the Synthesis of 3,4-Dihydropyran-2-Ones Organocatalyzed by N-Heterocyclic Carbenes.Molecules. 2023 Apr 26;28(9):3743. doi: 10.3390/molecules28093743. Molecules. 2023. PMID: 37175154 Free PMC article. Review.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
