Indium-mediated allylation of carbonyl compounds with an allylic bromide in aqueous media: anomalous syn-diastereoselectivity regardless of allylic bromide geometry

Loh, Teck‐Peng; Yin, Zheng; Song, Hongyan; Tan, Kee‐Leng

doi:10.1016/s0040-4039(02)02773-9

Cited by 32 publications

(13 citation statements)

References 14 publications

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“…The reaction afforded high syn selectivity regardless of the allylic bromide geometry. The enantioselective indium-mediated allylation was attempted and found to give the desired products in moderate yields with high syn selectivity and enantioselectivity . Indium trichloride-catalyzed indium-mediated allylation of dihydropyrans and dihydrofurans was reported in water.…”

Section: 11 Allylationmentioning

confidence: 99%

“…The enantioselective indium-mediated allylation was attempted and found to give the desired products in moderate yields with high syn selectivity and enantioselectivity. 323 Indium trichloride-catalyzed indium-mediated allylation of dihydropyrans and dihydrofurans was reported in water. This catalytic system afforded the allylated diols in moderate to high yields.…”

Section: Allylationmentioning

confidence: 99%

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Organic Reactions in Aqueous Media with a Focus on Carbon−Carbon Bond Formations: A Decade Update

2005

Chem. Rev.

2,171

641

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Section: 11 Allylationmentioning

confidence: 99%

Section: Allylationmentioning

confidence: 99%

Organic Reactions in Aqueous Media with a Focus on Carbon−Carbon Bond Formations: A Decade Update

2005

Chem. Rev.

2,171

641

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“…But, in some special cases, it was found that the utilization of ultrasonication, ,− or the addition of protic acid (e.g., HOAc/CF 3 COOH, − HCOOH, HCl, ,,− etc. ), Lewis acid (e.g., La(OTf) 3 , ,− Yb(OTf) 3 , HfCl 4 , − InCl 3 , − and In(OTf) 3 ), and Bu 4 NBr , as reaction additives, or the use of aqueous NH 4 Cl as reaction medium, ,,,− ,− also can lead to enhanced performance of indium-mediated allylation reactions, especially for less reactive allyl substrates.…”

Section: Allylindium Reagentsmentioning

confidence: 99%

Organoindium Reagents: The Preparation and Application in Organic Synthesis

et al. 2012

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allylation performed in aqueous media, an efficient synthesis of highly functionalized lactones was realized in good yields (64− 77%, Scheme 29). 238 However, the chirality installed during the first step almost had no influence on the second step, thus resulting in poor diastereoselectivity in the subsequent allylation reaction (1:1−2:1 dr).In situ formation of aldehyde from the oxidation of alcohol followed by one-pot indium-mediated allylation also provides an alternative method for the synthesis of homoallylic alcohol. Recently, Yadav and co-workers developed such a one-pot sequence by using chloramines-T (sodium salt of Nchlorotosylamide) as oxidant in the presence of a catalytic amount of FeCl 3 in CH 2 Cl 2 , giving rise to homoallylic alcohols in good to excellent yields (Scheme 30). 239 It is noteworthy that the generated byproduct of TsNH 2 (from the reduction of chloramines-T) may react with the in situ-formed aldehydes to give intermediates of N-tosylimines in the presence of 4 Å molecular sieve under refluxing; the thus-formed N-tosylimines subsequently underwent one-pot indium-mediated allylation to produce homoallylic amines in 60−80% yields. Later, a similar one-pot, two-step sequence for the synthesis of homoallylic alcohols via a galactose oxidase-mediated chemo-enzymatic oxidation of benzyl and cinnamyl alcohols to the corresponding Scheme 23 Scheme 24 Scheme 25 Scheme 26 Scheme 27 Scheme 28 Scheme 29 Scheme 30 Chemical Reviews Review dx.

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“…Indeed, such an enantioselective allylation was achieved in the presence of (-)-cinchonidine in the synthesis of a key precursor of antillatoxin. 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

161

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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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Indium-mediated allylation of carbonyl compounds with an allylic bromide in aqueous media: anomalous syn-diastereoselectivity regardless of allylic bromide geometry

Cited by 32 publications

References 14 publications

Organic Reactions in Aqueous Media with a Focus on Carbon−Carbon Bond Formations: A Decade Update

Organic Reactions in Aqueous Media with a Focus on Carbon−Carbon Bond Formations: A Decade Update

Organoindium Reagents: The Preparation and Application in Organic Synthesis

Recent Advances in Indium-Promoted Organic Reactions

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