Chiral synthesis via organoboranes. 27. Remarkably rapid and exceptionally enantioselective (approaching 100% ee) allylboration of representative aldehydes at -100.degree. under new, salt-free conditions

Racherla, Uday S.; Brown, Herbert C.

doi:10.1021/jo00001a072

Cited by 360 publications

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“…[3] As we now had sufficient quantitites of the key intermediate 2, we embarked on its straightforward transformation into the desired triols. Enantioselective allylboration with the quasi-enantiomeric allylboranes (allyl)B(2-isocaranyl) 2 and (allyl)B(4-isocaranyl) 2 , introduced by Brown and Racherla, [11] furnished the homoallylic alcohols 3 and 4 in moderate yields and good stereoselectivities (10 ± 15:1) (Scheme 2). The minor stereoisomers were removed by column chromatography.…”

Section: Resultsmentioning

confidence: 99%

General and Asymmetric Synthesis of Protected 1,3,5-Triols with Pendant Functional Groups

Schneider¹,

Rehfeuter²

1999

Chem. Eur. J.

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A stereoselective synthesis of enantiomerically pure 1,3,5-triols of any configuration has been developed. These triols carry suitable functional groups at the termini of the chain which should allow for easy and efficient coupling of two building blocks. The silyloxy-Cope rearrangement of syn-aldols was used to prepare a common advanced intermediate for the synthesis of all four stereoisomeric triols. Three synthetic operationsÐan allylboration, an oxidative desilylation, and a conjugate addition reactionÐwere employed to assemble the target molecules. Their terminal double bond may either be cleaved to give the corresponding aldehydes or oxidized to the methyl ketones in a Wacker process to provide access to two subunits for a coupling reaction.

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Section: Resultsmentioning

confidence: 99%

General and Asymmetric Synthesis of Protected 1,3,5-Triols with Pendant Functional Groups

Schneider¹,

Rehfeuter²

1999

Chem. Eur. J.

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“…Under salt-free conditions, B-allyldiisopinocampheylborane reacts with aldehydes at low temperatures (-100 °C) yielding homoallylic alcohols of high optical purity (up to 100% e.e.) [5]. …”

Section: Synthesis Of Syn-halohydrins and Cis-vinyloxiranesmentioning

confidence: 99%

B-Methoxydiisopinocampheylborane (Ipc2BOMe): A Pinene Based Auxiliary for Asymmetric C-C Bond-Forming Reactions

Hertweck

Boland²

1999

J. prakt. Chem.

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“…In the asymmetric addition of aldehydes to allylboronates, modifying different chiral auxiliaries resulted in good to excellent enantioselectivity (Roush et al, 1985a;Jadhav et al, 1986;Brown et al, 1990;Racherla and Brown, 1991). And tartrate esters modified allylboronates from several laboratories have been studied thoroughly because of its simple preparation and high enantioselectivity (Haruta et al, 1982;Roush et al, 1985b;Roush et al, 1988;Roush et al, 1990a).…”

Section: Introductionmentioning

confidence: 99%

Quantum chemical study on asymmetric allylation of benzaldehyde in the presence of chiral allylboronate

Chen

Chen²

2005

J Zheijang Univ Sci B

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Abstract:The quantum chemical method is employed to study the modified asymmetric allylation of benzaldehyde controlled by diisopropyl D-(-)-tartrate auxiliary. All the structures are optimized completely at the B3LYP/6-31G(d,p) level. The (R)-secondary alcohol can be achieved mainly through a six-membered ring chair-like transition state structure. From the relative reaction rates theory the main product configuration predicted is in agreement with the experiment result.

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Chiral synthesis via organoboranes. 27. Remarkably rapid and exceptionally enantioselective (approaching 100% ee) allylboration of representative aldehydes at -100.degree. under new, salt-free conditions

Cited by 360 publications

References 0 publications

General and Asymmetric Synthesis of Protected 1,3,5-Triols with Pendant Functional Groups

General and Asymmetric Synthesis of Protected 1,3,5-Triols with Pendant Functional Groups

B-Methoxydiisopinocampheylborane (Ipc2BOMe): A Pinene Based Auxiliary for Asymmetric C-C Bond-Forming Reactions

Quantum chemical study on asymmetric allylation of benzaldehyde in the presence of chiral allylboronate

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