Reduktive fragmentierung—III

Kraus, Wolfgang; Chassin, C.; Chassin, R.

doi:10.1016/s0040-4020(01)82901-x

Cited by 18 publications

(2 citation statements)

References 38 publications

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“…Reductive fragmentation was observed when bicyclic β-tosyloxyketone 144 or β-tosyloxyketal 147 was treated with LiAlH 4 to generate the exomethylene group in 146 and 149 (Scheme ). , …”

Section: Carbonyl Generating Grob Fragmentation Via Ring Cleavagementioning

confidence: 99%

“…44 Reductive fragmentation was observed when bicyclic β-tosyloxyketone 144 or β-tosyloxyketal 147 was treated with LiAlH 4 to generate the exomethylene group in 146 and 149 (Scheme 34). 45,46 Treatment of bicyclic β-tosyloxyketone 144 with methylmagnesium bromide in refluxing ether led to the fragmentation product 152 (Scheme 35). Similar results were observed with ketal 147 under the same conditions.…”

Section: β-Hydroxy Ketonesmentioning

confidence: 99%

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Synthetic Applications of the Carbonyl Generating Grob Fragmentation

2010

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Since 1996, he has been a full professor at the University of Vienna. His main research interests lie in the total synthesis of structurally and physiologically interesting natural products. Scheme 1. Early Fragmentation of Carbocation Observed Scheme 2. Fragmentation of Carbocation into Olefin and Ketone Scheme 3. Eschenmoser's Pioneering Work on Fragmentations Scheme 4. Spontaneous Fragmentation of β-Bromo Acid 19

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“…Reductive fragmentation was observed when bicyclic β-tosyloxyketone 144 or β-tosyloxyketal 147 was treated with LiAlH 4 to generate the exomethylene group in 146 and 149 (Scheme ). , …”

Section: Carbonyl Generating Grob Fragmentation Via Ring Cleavagementioning

confidence: 99%

Section: β-Hydroxy Ketonesmentioning

confidence: 99%

Synthetic Applications of the Carbonyl Generating Grob Fragmentation

2010

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Spectral and Chemical Evidence for the Structure of C‐Nor‐D‐Homoconessine

Woude

Hove

1973

Bulletin des Soc Chimique

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ABSTRACT. The rearranged product resulting from the action o f lithiwn alwniniwn hydride upon holarrhenine tosylate (IV) in ether solution has been tentatively formulated by Uffer as C-nor-D-homoconessine ( V ) .We ( V ) .In the course of his study on the alkaloid holarrhenine (I), Uffer2 hoped to achieve an immediate correlation between I and the parent Holarrhena alkaloid, conessine (II), through reductive removal of the oxygen function of holarrhenine (I). To this end, the crude tosylate (IV) of holarrhenine was allowed to react with lithium aluminium hydride in ether but a substance isomeric with conessine was obtained, for which structure V was proposed. Support to this assumption was provided by the solvolytic C-nor-D-homo rearrangement underwent by rockogenine 12-mesylate3. The author2 further supposed that the reaction involved the reduction of an intermediate enamine (VI) . -31 -

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Ungewöhnliche Reaktivität gespannter Brückenkopfderivate

Martı́nez

Fraile

1983

Chem. Ber.

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Unusual Reactivity of Strained Bridgehead Derivatives The solvolysis of 7,7‐dimethyl‐1, exo‐2‐bis(trifluoromethylsulfonyloxy)norbornane (5) in Et2O/I2Mg and 80% MeOH proceeds with formation of substituted 2‐norbornyl cations, yielding 1, exo‐2‐diiodo‐7,7‐dimethylnorbornane (9) and camphenilone (13), respectively. When the vic‐diiodide 9 is treated with LiAlH4/C6H6 partial epimerization to 1,endo‐2‐diiodo‐7,7‐dimethylnorbornane (12) is observed without reduction; this result is probably due to steric hindrance of the reactants.

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Reduktive fragmentierung—III

Cited by 18 publications

References 38 publications

Synthetic Applications of the Carbonyl Generating Grob Fragmentation

Synthetic Applications of the Carbonyl Generating Grob Fragmentation

Spectral and Chemical Evidence for the Structure of C‐Nor‐D‐Homoconessine

Ungewöhnliche Reaktivität gespannter Brückenkopfderivate

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