Tandem aldol-allylation reactions: Double CC bond formation using silicon-tethered dinucleophiles

frost, lisa; Smith, J. D.; Berrisford, David J.

doi:10.1016/s0040-4039(98)02126-1

Cited by 20 publications

(6 citation statements)

References 15 publications

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“…Application of the present method for synthesizing three lactone analogs 11, 12, and 13 was performed. Evaluation of these analogs revealed that cis-jasmone analog 12 has a notable perfume 25 and 23 are described in the electronic supporting information. † Ti-direct aldol-type addition of methyl propanoate to PhCHO or t-BuCHO (Scheme 1) Bu 3 N (475 lL, 2.0 mmol) and TiCl 4 (165 lL, 1.5 mmol) were successively added to a stirred solution of methyl propanoate (88 mg, 1.0 mmol) and an aldehyde (PhCHO; 127 mg or t-BuCHO; 103 mg, 1.2 mmol) in CH 2 Cl 2 (2.0 mL) at 0-5 • C under an Ar atmosphere, followed by being stirred at the same temp.…”

Section: (D) Synthesis Of Lactone [2(5h)-furanone] Analogs For Three ...mentioning

confidence: 99%

Ti-direct, powerful, stereoselective aldol-type additions of esters and thioesters to carbonyl compounds: application to the synthesis and evaluation of lactone analogs of jasmone perfumes

et al. 2007

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An efficient TiCl(4)-Et(3)N or Bu(3)N-promoted aldol-type addition of phenyl and thiophenyl esters or thioaryl esters with aldehydes and ketones was performed (total 46 examples). The present method is advantageous from atom-economical and cost-effective viewpoints; good to excellent yields, moderate to good syn-selectivity, substrate variations, reagent availability, and simple procedures. Utilizing the present reaction as the key step, an efficient short synthesis of three lactone [2(5H)-furanone] analogs of jasmine perfumes was performed. Among them, the lactone analog of cis-jasmone had a unique perfume property (tabac).

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Section: (D) Synthesis Of Lactone [2(5h)-furanone] Analogs For Three ...mentioning

confidence: 99%

Ti-direct, powerful, stereoselective aldol-type additions of esters and thioesters to carbonyl compounds: application to the synthesis and evaluation of lactone analogs of jasmone perfumes

et al. 2007

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“…Berrisford demonstrated that a silicon-tethered bisnucleophile could add to an external aldehyde electrophile in a cascade reaction. 4 More recently, Leighton has developed a powerful strategy to prepare polyol segments using similar silicon-tethered bis-nucleophiles. 5 The Mukaiyama aldol-Prins cyclization developed in our lab uses the reaction of a bis-nucleophile and an aldehyde to couple two fragments and build a ring.…”

mentioning

confidence: 99%

“…In most cases, the cyclization reaction is initiated by the addition of a proton or Lewis acid. Berrisford demonstrated that a silicon-tethered bis-nucleophile could add to an external aldehyde electrophile in a cascade reaction . More recently, Leighton has developed a powerful strategy to prepare polyol segments using similar silicon-tethered bis-nucleophiles .…”

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confidence: 99%

Titanium(IV)-Promoted Mukaiyama Aldol−Prins Cyclizations

2003

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[reaction: see text] A new version of the Mukaiyama aldol-Prins (MAP) cyclization has been developed. Unsaturated enol ethers such as 3 were found to couple with aldehydes in the presence of TiBr(4) to give 4-bromotetrahydropyran products. This cascade reaction sequence leads to the formation of two new carbon-carbon bonds, a ring, and three new stereogenic centers. We expect this reaction to be a powerful new tool in synthesis.

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“…139 A similar transformation was performed by Berrisford and co-workers. 140 Scheme 65 Tandem aldol-allylation reaction of allylenolsilanes. 139 This strategy was used also with (E)-and (Z)-crotylenolsilanes, also giving syn-1,3-diols.…”

Section: Scheme 62mentioning

confidence: 99%

Stereoselective Synthesis of 1,3-Diols

Bode¹,

Wolberg²,

Müller³

2006

Synthesis

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Many polyketide-derived natural products contain a synor anti-1,3-diol unit. No general and simple approach exists for the flexible synthesis of polyols and other polyketide-derived structural units, therefore a multitude of methods for the stereoselective synthesis of 1,3-diols has been developed. Asymmetric homogeneous and heterogeneous hydrogenation and diastereoselective reduction, chain elongation, enzymatic and nonenzymatic desymmetrization, or dynamic kinetic resolution are some of these methods. The development of different methods to synthesize these 1,3-diols stereoselectively is important, as often small structural changes in a molecule result in low yields or low stereoselectivity with a known method. This review article highlights some of the recent developments in this field.

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Tandem aldol-allylation reactions: Double CC bond formation using silicon-tethered dinucleophiles

Cited by 20 publications

References 15 publications

Ti-direct, powerful, stereoselective aldol-type additions of esters and thioesters to carbonyl compounds: application to the synthesis and evaluation of lactone analogs of jasmone perfumes

Ti-direct, powerful, stereoselective aldol-type additions of esters and thioesters to carbonyl compounds: application to the synthesis and evaluation of lactone analogs of jasmone perfumes

Titanium(IV)-Promoted Mukaiyama Aldol−Prins Cyclizations

Stereoselective Synthesis of 1,3-Diols

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