1,6-Conjugated addition-mediated [4 + 1] annulation: an approach to 2,3-dihydrobenzofurans
- 7 November 2017
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Organic Chemistry Frontiers
- Vol. 5 (4) , 623-628
Abstract
A formal 1,6-conjugated addition-mediated [4 + 1] annulation of ortho-hydroxyphenyl-substituted para-quinone methides with sulfonium or ammonium bromides has been described. This domino-type process offered an efficient method for the synthesis of 2,3-dihydrobenzofurans in good yields, exhibiting good functional group tolerance, scalability and high diastereoselectivity.Keywords
This publication has 56 references indexed in Scilit:
- Asymmetric Catalytic 1,6‐Conjugate Addition/Aromatization of para‐Quinone Methides: Enantioselective Introduction of Functionalized Diarylmethine Stereogenic CentersAngewandte Chemie International Edition, 2013
- Highly efficient oxidation of 2-imidazoline-5-carboxylic derivatives to imidazole-5-carboxylic derivatives by dioxygenTetrahedron, 2012
- Straightforward Synthesis of Enantiopure 2,3-Dihydrobenzofurans by a Sequential Stereoselective Biotransformation and Chemical Intramolecular CyclizationOrganic Letters, 2010
- AMP-Activated Protein Kinase (AMPK) Activation by Benzofurans and Coumestans Isolated from Erythrina abyssinicaJournal of Natural Products, 2010
- Asymmetric Organocatalytic Domino ReactionsAngewandte Chemie International Edition, 2007
- Enantioselective Catalytic Intramolecular Cyclopropanation using Modified Cinchona Alkaloid OrganocatalystsAngewandte Chemie International Edition, 2006
- A Rapid Synthesis of 2-Aryl-5-substituted-2,3-dihydrobenzofuransThe Journal of Organic Chemistry, 2005
- Enantioselective Organocatalytic Cyclopropanation via Ammonium YlidesAngewandte Chemie International Edition, 2004
- Phenolic and Antibacterial Constituents ofVahlia capensisPlanta Medica, 1997
- Studies in the synthesis of polycyclopentanoids: synthesis, oxa-di-π-methane rearrangement of annulated bicyclo[2.2.2]octenones and cyclopropane ring cleavage of tetracyclo[6.3.0.0.0]undecenonesJournal of the Chemical Society, Perkin Transactions 1, 1992