Metal-catalyzed [1,2]-alkyl shift in allenyl ketones: Synthesis of multisubstituted furans

Alexander S. Dudnik; Vladimir Gevorgyan

doi:10.1002/anie.200701128

Metal-catalyzed [1,2]-alkyl shift in allenyl ketones: Synthesis of multisubstituted furans

Alexander S. Dudnik, Vladimir Gevorgyan

Research output: Contribution to journal › Article › peer-review

201 Scopus citations

Abstract

(Chemical Equation Presented) Even fused furans can be prepared by cycloisomerization of substituted allenyl ketones. The cascade reaction involves a [1,2]-migration of alkyl or aryl groups in allenyl ketones as the key step. Facile reaction in the presence of cationic complexes, as well as migratory aptitude in the cycloisomerization of unsymmetrically substituted allenes, strongly supports an electrophilic mechanism for this transformation.

Original language	English (US)
Pages (from-to)	5195-5197
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	46
Issue number	27
DOIs	https://doi.org/10.1002/anie.200701128
State	Published - 2007
Externally published	Yes

Keywords

Allenyl ketones
Furans
Gold
Lewis acids
Rearrangment

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.200701128

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abstract = "(Chemical Equation Presented) Even fused furans can be prepared by cycloisomerization of substituted allenyl ketones. The cascade reaction involves a [1,2]-migration of alkyl or aryl groups in allenyl ketones as the key step. Facile reaction in the presence of cationic complexes, as well as migratory aptitude in the cycloisomerization of unsymmetrically substituted allenes, strongly supports an electrophilic mechanism for this transformation.",

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author = "Dudnik, {Alexander S.} and Vladimir Gevorgyan",

year = "2007",

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journal = "Angewandte Chemie - International Edition",

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T1 - Metal-catalyzed [1,2]-alkyl shift in allenyl ketones

T2 - Synthesis of multisubstituted furans

AU - Dudnik, Alexander S.

AU - Gevorgyan, Vladimir

PY - 2007

Y1 - 2007

N2 - (Chemical Equation Presented) Even fused furans can be prepared by cycloisomerization of substituted allenyl ketones. The cascade reaction involves a [1,2]-migration of alkyl or aryl groups in allenyl ketones as the key step. Facile reaction in the presence of cationic complexes, as well as migratory aptitude in the cycloisomerization of unsymmetrically substituted allenes, strongly supports an electrophilic mechanism for this transformation.

AB - (Chemical Equation Presented) Even fused furans can be prepared by cycloisomerization of substituted allenyl ketones. The cascade reaction involves a [1,2]-migration of alkyl or aryl groups in allenyl ketones as the key step. Facile reaction in the presence of cationic complexes, as well as migratory aptitude in the cycloisomerization of unsymmetrically substituted allenes, strongly supports an electrophilic mechanism for this transformation.

KW - Allenyl ketones

KW - Furans

KW - Gold

KW - Lewis acids

KW - Rearrangment

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JO - Angewandte Chemie - International Edition

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ER -

Metal-catalyzed [1,2]-alkyl shift in allenyl ketones: Synthesis of multisubstituted furans

Abstract

Keywords

ASJC Scopus subject areas

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