A Rapid and Stereoselective Route to the <i>trans</i>-Hydrindane Ring System

Khan, Faiz Ahmed; Satapathy, Rashmirekha; Savitha, G.

doi:10.1021/jo049615v

Cited by 15 publications

(5 citation statements)

References 20 publications

(9 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…During the course of the synthesis of a trans -hydrindane ring system, Khan and co-workers exploited the reaction of tetrabromo norbornyl aldehyde with propargyl bromide mediated by indium in DMF (Scheme ) . Although exclusive formation of homopropargyl alcohol was observed, the diastereoselectivity obtained was rather low (60:40 dr).…”

Section: Propargylindium and Allenylindium Reagentmentioning

confidence: 99%

“…Khan and co-workers explored the reaction of tetrabromo norbornyl aldehyde and allyl bromide mediated by indium, during the course of the synthesis of the trans-hydrindane ring system. 382 The reactions proceeded well in either aqueous media or DMSO to afford the allylated products in excellent yields with acceptable diastereoselectivities (Scheme 179).…”

Section: Nature Of Allylindium Reagentmentioning

confidence: 99%

See 1 more Smart Citation

Organoindium Reagents: The Preparation and Application in Organic Synthesis

et al. 2012

View full text Add to dashboard Cite

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.

show abstract

Section: Propargylindium and Allenylindium Reagentmentioning

confidence: 99%

Section: Nature Of Allylindium Reagentmentioning

confidence: 99%

Organoindium Reagents: The Preparation and Application in Organic Synthesis

et al. 2012

View full text Add to dashboard Cite

show abstract

“…In(0)-mediated allylation of tetrabromo norbornyl derivative 83a leads to the formation of 83b as the major diastereomer (Scheme 184). 167 The observation is explained by the preferential attack of allylindium from the less hindered Si-face of 83a. It may be noted that the product homoallyl derivatives are potential building blocks for the synthesis of steroidal and related bioactive molecules.…”

Section: Addition To Cdo Bondsmentioning

confidence: 99%

“…As pointed out earlier, another attractive feature of the indium metal mediated carbonyl allylation reaction is the ability to achieve a high degree of diastereoselection. − The latter depends upon the substituent(s) on the carbonyl and the allyl halide. For a succinct introduction of this aspect of the chemistry, the reader is referred to the review by Li and Chan .…”

Section: Allylindiummentioning

confidence: 99%