Allylic alkylation: nature of the nucleophile and application to prenylation

Trost, Barry M.; Weber, Lothar; Strege, Paul E.; Fullerton, Terry J.; Dietsche, Thomas J.

doi:10.1021/ja00479a026

Cited by 89 publications

(23 citation statements)

References 6 publications

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“…6,7 The chemoselectivity of the palladation reaction is noteworthy. Use of methyl phenylsulfinylacetate as nucleophile led to a one pot synthesis of dienoates (Scheme 3).…”

Section: Methodology Of Palladium Processesmentioning

confidence: 99%

Metal catalyzed allylic alkylation: its development in the Trost laboratories

Trost

2015

Tetrahedron

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191

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“…6,7 The chemoselectivity of the palladation reaction is noteworthy. Use of methyl phenylsulfinylacetate as nucleophile led to a one pot synthesis of dienoates (Scheme 3).…”

Section: Methodology Of Palladium Processesmentioning

confidence: 99%

Metal catalyzed allylic alkylation: its development in the Trost laboratories

Trost

2015

Tetrahedron

Self Cite

191

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“…The extension technique employed in the second route to [ 2 H 3 ]farnesol 29 (Scheme 5) was used, but with 33 as starting material. Spectroscopically, the isolated [ 2 H 3 ]GGA was identical to non-deuterated geranylgeraniol [21], apart from the lack of any signal from the terminal (E)-Me group. In the 2 H-NMR spectrum, the signal of the CD 3 group lies at 1.65 ppm.…”

mentioning

confidence: 98%

“…After decarboxylation of 34 with LiI/ NaCN [21], we were able to isolate only 44% of 35. We obtained double that yield, however, by using the method of Keinan and Eren [22].…”

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confidence: 99%

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Stereochemistry of Formation of theβ-Ring of Lycopene: Biosynthesis of (1R,1′R)-β,β-[16,16,16,16′,16′,16′-2H6]Carotene from [16,16,16,16′,16′,16′-2H6]Lycopene inFlavobacterium R 1560

Mohanty

Uebelhart

Eugster

2000

HCA

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Dedicated to Prof. Albert Eschenmoser on the occasion of his 75th birthday Incubation of deuteriated precursors in cultures of Flavobacterium produced specifically deuteriated carotenoids. Analysis of these led to several conclusions: i) Lycopene is a direct precursor of b,b-carotene. ii) Its terminal Me groups retain their integrity during cyclization: there is a stereospecific folding of the 1,5-diene. The Me(16,16') groups of lycopene become the Me(16,16') of b,b-carotene. Consequently, the folding must follow the C 2 (E,E) mode. iii) Incorporation of deuterium was sufficiently extensive to permit CD measurements on the isolated b,b-carotene, allowing its centers of chirality to be assigned as (1S,1'S). iv) The same chirality resulted from incorporation of [ 2 H 3 ]mevalonate into zeaxanthin. The syntheses of specifically deuteriated [ 2 H 3 ]GPP, [ 2 H 3 ]FPP, and [ 2 H 3 ]GG are described.

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“…7 Activation of these π-allyl complexes by phosphine ligands and subsequent nucleophilic attack by a stabilized carbanion lead to C-C bond formation in the allylic position. 6,8 The requirement of stoichiometric amounts of metal limits the synthetic utility of these reactions.…”

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confidence: 99%

Carbon−Carbon Bond Formation in Palladium(II)-Catalyzed Allylic Oxidation: A Novel Oxidative Carbocyclization of Allene-Substituted Olefins

2003

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A new efficient palladium(II)-catalyzed oxidative carbocyclization has been developed. It was found that allene-substituted olefins 1 cyclized in the presence of 1 mol % Pd(O2CCF3)2 and p-benzoquinone (2 equiv) to give bicyclic ring systems 2 in good to excellent yields. The cyclization constitutes a new type of carbon-carbon bond forming reaction between an allene and an olefin under oxidative conditions.

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Allylic alkylation: nature of the nucleophile and application to prenylation

Cited by 89 publications

References 6 publications

Metal catalyzed allylic alkylation: its development in the Trost laboratories

Metal catalyzed allylic alkylation: its development in the Trost laboratories

Stereochemistry of Formation of theβ-Ring of Lycopene: Biosynthesis of (1R,1′R)-β,β-[16,16,16,16′,16′,16′-2H6]Carotene from [16,16,16,16′,16′,16′-2H6]Lycopene inFlavobacterium R 1560

Carbon−Carbon Bond Formation in Palladium(II)-Catalyzed Allylic Oxidation: A Novel Oxidative Carbocyclization of Allene-Substituted Olefins

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