Reaction of Allylic-type Diindium Compounds with Electrophiles

Hirashita, T.; Arai, Shun; Mitsui, Kazuma; Makino, Hajime; Araki, Shuki

doi:10.1246/cl.2006.314

Cited by 4 publications

(4 citation statements)

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“…288 The substrate scope was further extended to the use of allylic system of 3-bromo-1-iodo-1-phenylpropene and 2,4-diiodobut-2-en-1-ol by Hirashita, Araki, and co-workers. 289 One notable feature is the further verification of the existence of diindium intermediates involved in the reaction of 3-bromo-1-iodo-1phenylpropene with aldehyde. As shown in Scheme 88, in addition to possible formation of routine monoallylation product C and/or D, the generation of two double-allylation products (A and B) has been observed in the use of 2 equiv of propionaldehyde (R = Et) as substrate.…”

Section: Nature Of Allylindium Reagentmentioning

confidence: 99%

“…The substrate scope was further extended to the use of allylic system of 3-bromo-1-iodo-1-phenylpropene and 2,4-diiodobut-2-en-1-ol by Hirashita, Araki, and co-workers . One notable feature is the further verification of the existence of diindium intermediates involved in the reaction of 3-bromo-1-iodo-1-phenylpropene with aldehyde.…”

Section: Allylindium Reagentsmentioning

confidence: 99%

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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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Section: Nature Of Allylindium Reagentmentioning

confidence: 99%

Section: Allylindium Reagentsmentioning

confidence: 99%

Organoindium Reagents: The Preparation and Application in Organic Synthesis

et al. 2012

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“…The efficient stereocontrolled construction of disubstituted and trisubstituted alkenes is a continuing challenge in organic synthesis. In 1982, Gras reported that trimethylsilyl iodide (TMSI) converted the inexpensive 2-butyn-1,4-diol 1 to the E isomer of 2 with high regiocontrol 1a. Curiously, no further exploration of 2 had been reported since that time 1b…”

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confidence: 99%

“…In 1982, Gras reported that trimethylsilyl iodide (TMSI) converted the inexpensive 2-butyn-1,4-diol 1 to the E isomer of 2 with high regiocontrol 1a. Curiously, no further exploration of 2 had been reported since that time 1b) that the conversion of 1 to 2 proceeded efficiently using in situ generated 2 TMSI; however, the product formed was actually the Z isomer.…”

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Preparation of 2-Iodo Allylic Alcohols from 2-Butyn-1,4-diol

et al. 2008

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