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Tetrahedron Letters

Volumn 57, Issue 21, 2016, Pages 2269-2272

Nucleophilic β-alkenylation of N-alkoxyenamines: An umpolung strategy for the preparation of β,γ-unsaturated ketones

(4) Nandi, Raj Kumar a Takeda, Norihiko a Ueda, Masafumi a Miyata, Okiko a

a KOBE PHARMACEUTICAL UNIVERSITY (Japan)

Author keywords

Alkenyl aluminum reagent; Isoxazolidine; N Alkoxyenamine; Umpolung; , Unsaturated ketone

Indexed keywords

ALUMINUM; BETA,GAMMA UNSATURATED KETONE; ENAMINE; ISOXAZOLIDINE DERIVATIVE; KETONE; N ALKOXYENAMINE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; BETA ALKENYLATION; CHEMICAL REACTION; NUCLEOPHILICITY; REACTION ANALYSIS; SYNTHESIS;

EID: 84964751095 PISSN: 00404039 EISSN: 18733581 Source Type: Journal
DOI: 10.1016/j.tetlet.2016.04.033 Document Type: Article

Times cited : (8)

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- 13 (0.60 M in n-hexane, 3.0 mL, 1.5 mmol) was added dropwise to the filtrate at 0 °C. After stirring at 0 °C for 1 h, the reaction was quenched with aqueous Rochelle's salt (1.3 M).
- + 169.1586, found 169.1587.

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- The reaction of 5a with 7a (3 equiv) in the presence of isoxazolidine (2 equiv) at 0 °C for 1 h gave β,γ-unsaturated ketone 8aa in 21% yield (one-pot procedure).
- The reaction of 5a with 7a (3 equiv) in the presence of isoxazolidine (2 equiv) at 0 °C for 1 h gave β,γ-unsaturated ketone 8aa in 21% yield (one-pot procedure).

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- For the umpolung β-alkenylation of N-alkoxyenamine 6a with diisobutyl(styryl)aluminum [prepared in situ by Ni-catalyzed β-hydroalumination of phenylacetylene with DIBAL-H], α-alkenylated product carrying styryl group was obtained in 11% yield. When other alkenyl aluminum reagent [prepared in situ by hydroalumination of 1-phenyl-2-(trimethylsilyl)acetylene with DIBAL-H] was used, a trace amount of α-alkenylated product was detected.
- For the umpolung β-alkenylation of N-alkoxyenamine 6a with diisobutyl(styryl)aluminum [prepared in situ by Ni-catalyzed β-hydroalumination of phenylacetylene with DIBAL-H], α-alkenylated product carrying styryl group was obtained in 11% yield. When other alkenyl aluminum reagent [prepared in situ by hydroalumination of 1-phenyl-2-(trimethylsilyl)acetylene with DIBAL-H] was used, a trace amount of α-alkenylated product was detected.

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