Stability and oxidative coupling of chiral vinyl- and cyclopropylcopper reagents. Formation of a novel dissymmetric diene

Walborsky, H. M.; Banks, R. Bruce; Banks, Mona-Lisa; Duraisamy, M.

doi:10.1021/om00064a017

Cited by 20 publications

(4 citation statements)

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“…Silylation of the derived cyclopropylmethanol under standard conditions furnished stannane 8 which was trans metalated with sec -BuLi. The newly generated lithium anion was added to [ICuPBu 3 ] 4 and then subjected to an O 2 -induced dimerization at low temperature to give syn-trans,trans -bicyclopropane 9 (98% ee 18 ), [α] D 23 −41.5° ( c 0.23, absolute EtOH). The enrichment in enantiomeric composition is a manifestation of the statistical distribution of products and represents a variant of the Horeau amplification principle…”

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confidence: 99%

Synthesis of the Polycyclopropane Antibiotic FR-900848 via the Horeau Gambit

Falck

Mekonnen²,

Yu³

et al. 1996

J. Am. Chem. Soc.

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confidence: 99%

Synthesis of the Polycyclopropane Antibiotic FR-900848 via the Horeau Gambit

Falck

Mekonnen²,

Yu³

et al. 1996

J. Am. Chem. Soc.

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“…The group illustrated a variant of the Horeau principle, leading to material of high enantiomeric enrichment: Charette cyclopropanation of stannane 76 , , followed by protecting of the primary alcohol, furnished compound 77 in high yield and good selectivity (∼88% ee) (Scheme ). After transmetalation, an oxygen-induced dimerization , at low temperature provided the trans − syn − trans -bicyclopropane 78 in good yieldusing the Horeau amplification principlewith a dramatically improved enantiomeric excess (98% ee). It is noteworthy that Itoh et al also successfully dimerized enantiomerically pure (through kinetic enzymatic resolution , ) tributylstannylcyclopropanes directly .…”

Section: Synthesis By Falck Et Almentioning

confidence: 99%

Synthesis and Properties of Oligocyclopropyl-Containing Natural Products and Model Compounds

Pietruszka

2003

Chem. Rev.

255

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“…Most organometallic reagents react with air, whereby either alkanes are formed by dimerization of the metal-bound alkyl groups (cuprates often react this way [80]) or peroxides or alcohols are formed [81,82]. Most organometallic reagents react with air, whereby either alkanes are formed by dimerization of the metal-bound alkyl groups (cuprates often react this way [80]) or peroxides or alcohols are formed [81,82].…”

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confidence: 99%

The Stability of Organic Compounds

Dörwald

2004

Side Reactions in Organic Synthesis

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Scheme 3.2). Reversible reactions are, for this reason, not usually suitable for the formation of strained bonds.Strained cyclohexenes, such as norbornene derivatives, can undergo retro-Diels-Alder reactions even at relatively low temperatures, and this reaction can be used to prepare 1,3-dienes and alkenes (e.g. synthesis of cyclopentadiene by thermolysis of 36 Scheme 3.1. Thermal decomposition of strained compounds [1-8]. Strained Bondsdicyclopentadiene at approximately 160 C). In the example shown in Scheme 3.3 (first reaction) an enantiomerically pure bicyclic cyclohexanone is prepared from a readily available natural product. The radical scavenger is added to the starting material to prevent oxidation.The second example in Scheme 3.3 illustrates the reversibility of aldol additions. The starting bicyclic ketone is a vinylogous aldol which upon treatment with base undergoes retro-aldol addition by cleavage of a strained, hexasubstituted ethane sub-37 Scheme 3.2. Fragmentation via retro-Diels-Alder cycloaddition and retro-aldol addition. Scheme 3.3. Retro-Diels-Alder [9], retro-aldol [10] and retro-Mannich reaction [11] of strained substrates. 39 Scheme 3.5. Dealkylative oxidation of dihydropyridines [16] and reductive cleavage of cyclobutanes [17]. Scheme 3.6. Oxidation of a strained alkene by air [20] and relative rates of epoxidation of various cyclic alkenes [21]. 42 Scheme 3.10. Facile nucleophilic substitutions at 4-hydroxybenzyl derivatives [31-33].Scheme 3.11. Rearrangement of a-amino ketones [34].

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Stability and oxidative coupling of chiral vinyl- and cyclopropylcopper reagents. Formation of a novel dissymmetric diene

Cited by 20 publications

References 2 publications

Synthesis of the Polycyclopropane Antibiotic FR-900848 via the Horeau Gambit

Synthesis of the Polycyclopropane Antibiotic FR-900848 via the Horeau Gambit

Synthesis and Properties of Oligocyclopropyl-Containing Natural Products and Model Compounds

The Stability of Organic Compounds

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