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Search for "allylboration" in Full Text gives 12 result(s) in Beilstein Journal of Organic Chemistry.

Cu–Bpin-mediated dimerization of 4,4-dichloro-2-butenoic acid derivatives enables the synthesis of densely functionalized cyclopropanes

  • Patricia Gómez-Roibás,
  • Andrea Chaves-Pouso and
  • Martín Fañanás-Mastral

Beilstein J. Org. Chem. 2025, 21, 877–883, doi:10.3762/bjoc.21.71

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  • bearing aromatic and aliphatic substituents efficiently provided the allylboration product (Scheme 1a), the use of ester derivative 1 under same reaction conditions led to the formation of an unexpected product arising from the coupling of two dichloride molecules with no alkyne incorporation (Scheme 1b
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Letter
Published 05 May 2025

Recent advances in allylation of chiral secondary alkylcopper species

  • Minjae Kim,
  • Gwanggyun Kim,
  • Doyoon Kim,
  • Jun Hee Lee and
  • Seung Hwan Cho

Beilstein J. Org. Chem. 2025, 21, 639–658, doi:10.3762/bjoc.21.51

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  • electrophiles 11. Enantioselective hydroallylation and allylboration of styrenes A significant advance in the CuH-catalyzed enantioselective allylic substitution was reported by Buchwald and co-workers in 2016, who demonstrated the first successful hydroallylation of vinylarenes 30 using allylic phosphate
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Review
Published 20 Mar 2025

Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

  • Austin Pounder,
  • Eric Neufeld,
  • Peter Myler and
  • William Tam

Beilstein J. Org. Chem. 2023, 19, 487–540, doi:10.3762/bjoc.19.38

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Published 24 Apr 2023

Vicinal ketoesters – key intermediates in the total synthesis of natural products

  • Marc Paul Beller and
  • Ulrich Koert

Beilstein J. Org. Chem. 2022, 18, 1236–1248, doi:10.3762/bjoc.18.129

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  • reactivity in their synthesis of (+)-awajanomycin (92), a marine natural product with a γ-lactone-δ-lactam core structure (Scheme 15) [30][31]. Key step was an asymmetric allylboration of diethyl mesoxalate (90a) with boronate 89, which was easily accessible through a Matteson homologation of dichloromethyl
  • ]. Enantioselective aldol reaction using an α-ketoester in the synthesis of (−)-irofulven (87) [29]. Allylboration of a mesoxalic acid ester in the synthesis of (+)-awajanomycin (92) [30][31]. Condensation of a diamine with mesoxolate in the synthesis of (−)-aplaminal (96) [32]. Synthesis of mesoxalic ester amide 102
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Published 15 Sep 2022

Stereodivergent approach in the protected glycal synthesis of L-vancosamine, L-saccharosamine, L-daunosamine and L-ristosamine involving a ring-closing metathesis step

  • Pierre-Antoine Nocquet,
  • Aurélie Macé,
  • Frédéric Legros,
  • Jacques Lebreton,
  • Gilles Dujardin,
  • Sylvain Collet,
  • Arnaud Martel,
  • Bertrand Carboni and
  • François Carreaux

Beilstein J. Org. Chem. 2018, 14, 2949–2955, doi:10.3762/bjoc.14.274

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  • corresponding alkenes 13a,b in 90% and 63% yield, respectively, over two steps. Alternatively, we envisioned that, from the same α-substituted chiral aldehyde 5, compound 13b could be obtained in a more straightforward manner employing a strategy based on a diastereoselective allylboration reaction (Scheme 2
  • metathesis of vinyl ethers as key step for the preparation of several carbamate-protected 3-aminoglycals. Evans aldol reaction for the preparation of diastereomeric compounds 13a and 13b. Alternative preparation of 13b based on a diastereoselective allylboration. O-Vinylation-ring-closing metathesis sequence
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Published 29 Nov 2018

The chemistry and biology of mycolactones

  • Matthias Gehringer and
  • Karl-Heinz Altmann

Beilstein J. Org. Chem. 2017, 13, 1596–1660, doi:10.3762/bjoc.13.159

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Published 11 Aug 2017

Boron-substituted 1,3-dienes and heterodienes as key elements in multicomponent processes

  • Ludovic Eberlin,
  • Fabien Tripoteau,
  • François Carreaux,
  • Andrew Whiting and
  • Bertrand Carboni

Beilstein J. Org. Chem. 2014, 10, 237–250, doi:10.3762/bjoc.10.19

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  • tools in synthetic organic chemistry. The most significant recent results and developments obtained in this area are reported in this review. Keywords: allylboration; boron compounds; Diels–Alder; 1,3-dienes; multicomponent reactions; Petasis borono–Mannich; Suzuki couplings; Introduction
  • described in 1972 by Mikhailov and co-workers [29], and it was only fifteen years later that the groups of Vaultier and Hoffmann highlighted the real potential of these compounds in tandem cycloaddition [4 + 2]/allylboration processes [30]. These dienes reacted with activated dienophiles, such as maleic
  • /allylboration reactions [41]. In the case of the 4-methoxy-substituted diene, if the first step occurred at 80 °C in toluene, it was impossible to obtain the allylation products, even by heating at higher temperature or by activation with EtAlCl2. By contrast, with the 3-OTES derivative, bicyclic, three
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Published 22 Jan 2014

Aryl nitrile oxide cycloaddition reactions in the presence of pinacol boronic acid ester

  • Sarah L. Harding,
  • Sebastian M. Marcuccio and
  • G. Paul Savage

Beilstein J. Org. Chem. 2012, 8, 606–612, doi:10.3762/bjoc.8.67

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  • esters in organic synthesis is demonstrated by their use as key intermediates in transition-metal-catalysed bond-forming reactions [6], which include the Miyaura–Suzuki coupling reaction [7], copper-catalysed heteroatom arylation [8], allylboration [9], and the Petasis reaction [10]. Aryl boronic esters
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Published 19 Apr 2012

Directed ortho,ortho'-dimetalation of hydrobenzoin: Rapid access to hydrobenzoin derivatives useful for asymmetric synthesis

  • Inhee Cho,
  • Labros Meimetis,
  • Lee Belding,
  • Michael J. Katz,
  • Travis Dudding and
  • Robert Britton

Beilstein J. Org. Chem. 2011, 7, 1315–1322, doi:10.3762/bjoc.7.154

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  • hydrobenzoin·SnCl4 complex 5 promotes the allylboration of hydrocinnamaldehyde with modest enantioselectivity (26% ee) [3], and a hydrobenzoin–ytterbium complex was found to catalyze asymmetric aldol/Evans–Tishchenko reactions [5]. Moreover, the hydrobenzoin dimethyl ether 7 was shown to direct the asymmetric
  • parent diol 3 [3][14]. For example, the addition of cyclooctyl rings to the ortho and ortho' positions of the hydrobenzoin·SnCl4 complex (i.e., Vivol·SnCl4 (6)) leads to a dramatic improvement in enantioselectivity in the allylboration of hydrocinnamaldehyde (93% ee) [3]. Unfortunately, while (R,R)- and
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Published 22 Sep 2011

Recent progress on the total synthesis of acetogenins from Annonaceae

  • Nianguang Li,
  • Zhihao Shi,
  • Yuping Tang,
  • Jianwei Chen and
  • Xiang Li

Beilstein J. Org. Chem. 2008, 4, No. 48, doi:10.3762/bjoc.4.48

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Published 05 Dec 2008

An asymmetric synthesis of all stereoisomers of piclavines A1-4 using an iterative asymmetric dihydroxylation

  • Yukako Saito,
  • Naoki Okamoto and
  • Hiroki Takahata

Beilstein J. Org. Chem. 2007, 3, No. 37, doi:10.1186/1860-5397-3-37

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  • challenge. Our interest in this field has been focused on potential strategies based on the enantiomeric enhancement caused by the twofold or more application of the Sharpless asymmetric dihydroxylation (AD) [5][6] or Brown's asymmetric allylboration[7] reactions. In general, the enantiomeric excesses (ees
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Published 29 Oct 2007

Synthesis of 2,6-trans- disubstituted 5,6-dihydropyrans from (Z)-1,5-syn-endiols

  • Eric M. Flamme and
  • William R. Roush

Beilstein J. Org. Chem. 2005, 1, No. 7, doi:10.1186/1860-5397-1-7

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  • silylation of the allylic alcohol unit followed by mesylate formation and base-promoted nucleophilic displacement. Findings We recently reported a one-pot double allylboration reaction sequence which provides (Z)-1,5-syn-endiols from simple aldehyde starting materials with excellent diastereo- and
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Preliminary Communication
Published 26 Aug 2005
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