Stereoselective synthesis of 3,4-disubstituted tetrahydrofurans and 2,3,4-trisubstituted tetrahydrofurans using an intramolecular allylation strategy employing allylsilanes

Jervis, P. J.; Kariuki, Benson M.; Cox, Liam R.

doi:10.1016/j.tetlet.2008.02.088

Cited by 9 publications

(2 citation statements)

References 27 publications

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“…In these processes, an allyl silane and a carbonyl group of an aldehyde are involved in an intramolecular allylation promoted by a Brønsted acid. When the optimized reaction conditions were applied to the polyfunctionalized enantiomerically pure aldehyde 6 , derived from ( S )-ethyl mandelate, a trisubstituted tetrahydrofuran was produced with good 1,2-stereoinduction (Scheme ) …”

Section: Substrate Controlmentioning

confidence: 99%

Diastereoselective Allylation of Carbonyl Compounds and Imines: Application to the Synthesis of Natural Products

2013

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2.2. Chiral Imines and Imine Derivatives 2.2.1. Imines and Imine Derivatives from Chiral Carbonyl Compounds. Chiral α-oxysubstituted aldehydes were used by Kobayashi and co-workers in a three-component reaction with allylboropinacolate and ammonia in ethanol. The corresponding homoallylic primary amines were obtained with good to high syn diastereofacial selectivities (Scheme 5). 20 The precise reaction mechanism was unclear. Preformation of N-Scheme 3 Scheme 4 Scheme 5 Chemical Reviews Review dx.

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Section: Substrate Controlmentioning

confidence: 99%

Diastereoselective Allylation of Carbonyl Compounds and Imines: Application to the Synthesis of Natural Products

2013

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“…Among them, we can highlight the Hosomi-Sakurai reaction, recently applied by Cox and co-workers to the synthesis of 2,3,4-trisubstituted THF with moderate to good diastereoselectivities. 145 Still starting from an acyclic ether, the C-C bond can also be formed by a domino Heck-Suzuki reaction, as shown by Braun et al, 146 by reaction of a carbene with a benzylic ether, 147 following an indium-catalyzed hydrative cyclization of diyne. 148 Another strategy developed by Rovis and co-workers involves a cyclic acetal, which is activated by a Lewis acid to perform a ring contraction by Mukaiyama-aldol reaction leading M A N U S C R I P T A C C E P T E D ACCEPTED MANUSCRIPT to 2,3,4-trisubstituted THF.…”

Section: Miscellaneousmentioning

confidence: 97%

Recent advances in the synthesis of tetrahydrofurans and applications in total synthesis

et al. 2016

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Mousseron. His research interests include the total synthesis of oxygenated cyclic and non cyclic metabolites of polyunsaturated fatty acids, mainly leukotrienes, iso-, phyto-and neuroprostanes, as well as dihydroxylated PUFAs and more recently lipophenols and the understanding of the role of such bioactive lipids and lipophenols by developing collaborations with chemists, biochemists, biologists and clinicians across the world. Jean-Marie Galano studied chemistry at Paul Cézanne Université Marseille and obtained his PhD under the supervision of Honoré Monti in 2001. He then moved to the University of Oxford to pursue a postdoctoral fellowship with David H. Hodgson on the development of new methods for the total synthesis of natural products. In October 2005 he joined the CNRS as a Chargé de Recherche at Université of Montpellier. His research focuses on the total synthesis and discovery of new lipid metabolites, and to discover their potential implications in human health. AbstractMany natural products contain tetrahydrofuran (THF) moieties. Those molecules, often biologically active, may be structurally diverse, e.g. cis or trans THF, mono-, di-, tri-or tetrasubstituted on the furan ring. Thus, the construction of THF is of great interest for the community of organic chemists; especially in developing new methodologies, and applying them in the total synthesis of natural products. The aim of this review is to report recent advances in the field of THF synthesis, as well as the application of these methods to the synthesis of bioactive compounds.

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ChemInform Abstract: Stereoselective Synthesis of 3,4‐Disubstituted Tetrahydrofurans and 2,3,4‐Trisubstituted Tetrahydrofurans Using an Intramolecular Allylation Strategy Employing Allylsilanes.

2008

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Stereoselective synthesis of 3,4-disubstituted tetrahydrofurans and 2,3,4-trisubstituted tetrahydrofurans using an intramolecular allylation strategy employing allylsilanes

Cited by 9 publications

References 27 publications

Diastereoselective Allylation of Carbonyl Compounds and Imines: Application to the Synthesis of Natural Products

Diastereoselective Allylation of Carbonyl Compounds and Imines: Application to the Synthesis of Natural Products

Recent advances in the synthesis of tetrahydrofurans and applications in total synthesis

ChemInform Abstract: Stereoselective Synthesis of 3,4‐Disubstituted Tetrahydrofurans and 2,3,4‐Trisubstituted Tetrahydrofurans Using an Intramolecular Allylation Strategy Employing Allylsilanes.

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