Regio- and stereo-selectivity in uncatalysed and catalysed Diels–Alder reactions of allenic esters with furan and 2-methylfuran
- 1 January 1990
- journal article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 8,p. 2185-2192
- https://doi.org/10.1039/p19900002185
Abstract
Complete regio- and stereo-selectivity in both uncatalysed and catalysedt Diels–Alder additions of furan to the allenic esters (1a–e), and of 2-methylfuran to the allenic esters (1b, c) has been determined through detailed 1H and 13C NMR spectral investigations. Eu(fod)3 and Pr(fod)3 have been found to be very useful mild Lewis acid catalysts for these cycloadditions; several mol % of these reagents significantly enhance the selectivity and yield of these reactions without adversely affecting the fragile functionalities. A rationalization of the observed regio- and stereoselectivity and reactivity profile, based on the stereoelectronic factors operating in the transition states is given.Keywords
This publication has 57 references indexed in Scilit:
- Reagent design and study of allene as a promising class of reagents (synthons) for cycloaddition. The site-selective and regioselective Diels-Alder reactions of (phenylsulfonyl)propadiene and alkylation of the adductsThe Journal of Organic Chemistry, 1985
- Recent developments in allene chemistryTetrahedron, 1984
- Asymmetric diels-alder reaction of a chiral allenic ester : enantioselective synthesis of (−)-β-santaleneTetrahedron Letters, 1983
- The Diels–Alder reaction of furan and phenylsulphonylpropadiene. The simple base induced rearrangement of 3-methylene-2-endo-phenylsulphonyl-7-oxabicyclo[2.2.1]hept-5-eneJournal of the Chemical Society, Chemical Communications, 1983
- Bicyclo[2.2.2]octanes from Allenecarboxylic Acid Esters and CyclohexadienolatesAngewandte Chemie International Edition in English, 1982
- A General Route to Homophthalic Acid Derivatives - Valuable Precursors to Isoquinolinones, Dihydronaphthols and IsocoumarinsSynthetic Communications, 1978
- An Approach to the Skeleton of Rauwolfia Alkaloids: A General Synthesis of 3,8-Epoxy-7-keto-6-oxabicyclo[3.2.1]octane DerivativesHETEROCYCLES, 1978
- 1,3-Diethoxycarbonylallene: an active dienophile and ethoxycarbonylketen equivalent in the synthesis of antibiotic C-nucleosidesJournal of the Chemical Society, Chemical Communications, 1977
- The total synthesis of fulvoplumierinJournal of the American Chemical Society, 1968
- The Absolute Configuration of Pentadiendioic AcidJournal of the American Chemical Society, 1964