One-pot synthesis of aromatic homoallylic alcohols from aldehydes and Grignard reagents promoted by Titanium(IV) tetraisopropanolate

Song, Xiao-Nan; Liu, Lu; Hua, Si-Kai; Chen, Weidong; Ren, Jiangmeng

doi:10.1016/j.tet.2014.08.070

Tetrahedron

2014

DOI: 10.1016/j.tet.2014.08.070

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One-pot synthesis of aromatic homoallylic alcohols from aldehydes and Grignard reagents promoted by Titanium(IV) tetraisopropanolate

Xiao-Nan Song¹,

Lu Liu²,

Si-Kai Hua³

et al.

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Cited by 3 publications

(1 citation statement)

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“…The crude material was purified by flash chromatography (10% Et 2 O/n-hexane) to give alcohol 5h (57.2 mg, 76%) as a white solid. The data are consistent with the literature 39. R f = 0.30 (10% Et 2 O/n-hexane); mp 123-125 °C (petroleum ether).…”

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confidence: 90%

Nickel-Catalysed Allylboration of Aldehydes

Dennis¹,

Robertson²,

Partridge³

2020

Synthesis

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confidence: 90%

Nickel-Catalysed Allylboration of Aldehydes

Dennis¹,

Robertson²,

Partridge³

2020

Synthesis

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ChemInform Abstract: One‐Pot Synthesis of Aromatic Homoallylic Alcohols from Aldehydes and Grignard Reagents Promoted by Titanium(IV) Tetraisopropanolate.

et al. 2015

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Zinc-mediated α-regioselective Barbier-type cinnamylation reactions of aldehydes, ketones and esters

Zhao

Gao

et al. 2017

Org. Biomol. Chem.

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We report a simple, efficient, and general method for the zinc-mediated regioselective cinnamylation of aldehydes and ketones under Barbier-type conditions in a one-pot synthesis affording the corresponding α-cinnamylated alcohols in moderate to excellent yields. Compared to the literature procedures, this approach is operationally simple, uses simple reactants, and provides direct access to linear α-cinnamylated alcohols with excellent regioselectivity. Experimental results suggest that the reactions proceed through the radical pathway. In addition, the reaction was found to be scalable to the gram-scale and the one-pot protocol is also applicable to less reactive esters leading to bishomoallylic alcohols which were valuable intermediates for desymmetrizing intramolecular Heck cyclization, allowing for the elaboration to functionalized building blocks.

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One-pot synthesis of aromatic homoallylic alcohols from aldehydes and Grignard reagents promoted by Titanium(IV) tetraisopropanolate

Cited by 3 publications

References 23 publications

Nickel-Catalysed Allylboration of Aldehydes

Nickel-Catalysed Allylboration of Aldehydes

ChemInform Abstract: One‐Pot Synthesis of Aromatic Homoallylic Alcohols from Aldehydes and Grignard Reagents Promoted by Titanium(IV) Tetraisopropanolate.

Zinc-mediated α-regioselective Barbier-type cinnamylation reactions of aldehydes, ketones and esters

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