Indium-mediated Barbier-type allylation of aldehydes as a convenient method for the highly enantioselective synthesis of homoallylic alcohols

Hirayama, Lacie C.; Gamsey, Soya; Knueppel, Daniel; Steiner, Derek; DeLaTorre, Kelly; Singaram, Bakthan

doi:10.1016/j.tetlet.2005.01.169

Cited by 48 publications

(26 citation statements)

References 45 publications

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“…43 More recently, a chiral ligand bearing vicinal hydroxyl and amino groups (10) was found to be efficient in the indium-mediated allylation of both aromatic and aliphatic aldehydes (Scheme 8). 44 Scheme 5 Rearrangement of g-adducts into a-adducts…”

Section: Scheme 6 Indium-mediated Allylation With 3-bromopropenyl Acementioning

confidence: 99%

Recent Advances in Indium-Promoted Organic Reactions

Augé¹,

Lubin‐Germain²,

Uziel³

2007

Synthesis

162

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I n d i u m -P r o m o t e d O r g a n i c R e a c t i o n sAbstract: This review deals with organic reactions which are promoted by indium metal or indium salts, with a focus on recent advances in stoichiometric and catalytic pathways. Applications to transmetalations, cross-coupling reactions and carboindation, in which an organoindium species may be postulated, are highlighted, as well as the reactions in which a radical is the key intermediate. Special attention is placed on the role of indium metal as a reducer, and on the Lewis acidity of indium salts in catalytic processes.

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Section: Scheme 6 Indium-mediated Allylation With 3-bromopropenyl Acementioning

confidence: 99%

Recent Advances in Indium-Promoted Organic Reactions

Augé¹,

Lubin‐Germain²,

Uziel³

2007

Synthesis

162

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“…The asymmetric version of this synthesis would have to be considered if we were to prove the absolute configuration of the two chiral centers. One of our intermediates, alcohol 27, could be obtained in its chiral form by an asymmetric allylation under Barbier conditions with the addition of chiral auxiliaries such as amino alcohols, [45] camphor derivatives, [46] or cinchonine. [47] Oxidation of the alcohol function and subsequent Corey-Bakshi-Shibata [48] reduction may be another possibility for controlling the center at C8.…”

Section: Discussionmentioning

confidence: 99%

Towards the Synthesis of the 4,19‐Diol Derivative of (–)‐Mycothiazole: Synthesis of a Potential Key Intermediate

Batt

Fache

2011

Eur J Org Chem

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The synthesis of a potential key intermediate for the synthesis of the 4,19‐diol derivative of (–)‐mycothiazole using convergent strategies is described in this paper. Several approaches have been tested, including cross metathesis and a Julia–Kocienski olefination. Finally, the formation of the 1,1‐dialkyl‐1,2‐ethanediol motif through C4–C5 bond construction was realized by nucleophilic addition of a vinyl iodide derivative to a keto ester after halogen/lithium exchange followed by reduction of the resulting hydroxy ester.

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“…( 1)], its asymmetric variant was not simply accessible. We envisaged to use an asymmetric Barbier-type addition by applying a chiral indium reagent, [14] or a coppercatalyzed enantioselective allylation employing allylboron reagents. [15] Unfortunately, extensive attempts failed to give a satisfactory result.…”

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confidence: 99%