NHC-Catalyzed Reactions of Aryloxyacetaldehydes: A Domino Elimination/Conjugate Addition/Acylation Process for the Synthesis of Substituted Coumarins

Eric M Phillips; Manabu Wadamoto; Howard S Roth; Andrew W Ott; Karl A Scheidt

doi:10.1021/ol802448c

NHC-Catalyzed Reactions of Aryloxyacetaldehydes: A Domino Elimination/Conjugate Addition/Acylation Process for the Synthesis of Substituted Coumarins

Eric M Phillips, Manabu Wadamoto, Howard S Roth, Andrew W Ott, Karl A Scheidt

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Abstract

N-Heterocyclic carbenes (NHCs) catalyze a domino Michael addition/acylation reaction to form 3,4-dihydrocoumarins. The reaction proceeds through addition of the NHC to an aryloxyaldehyde followed by elimination of a phenoxide leaving group, generating an enol intermediate. This transient nucleophile generated in situ performs a 1,4-addition onto a conjugate acceptor, and the carbene catalyst is regenerated upon acylation of the phenoxide anion resulting in formation of 3,4-dihydrocoumarins.

Original language	English
Pages (from-to)	105-108
Journal	Organic Letters
Volume	11
DOIs	https://doi.org/10.1021/ol802448c
State	Published - 2009

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title = "NHC-Catalyzed Reactions of Aryloxyacetaldehydes: A Domino Elimination/Conjugate Addition/Acylation Process for the Synthesis of Substituted Coumarins",

abstract = "N-Heterocyclic carbenes (NHCs) catalyze a domino Michael addition/acylation reaction to form 3,4-dihydrocoumarins. The reaction proceeds through addition of the NHC to an aryloxyaldehyde followed by elimination of a phenoxide leaving group, generating an enol intermediate. This transient nucleophile generated in situ performs a 1,4-addition onto a conjugate acceptor, and the carbene catalyst is regenerated upon acylation of the phenoxide anion resulting in formation of 3,4-dihydrocoumarins.",

author = "Phillips, {Eric M} and Manabu Wadamoto and Roth, {Howard S} and Ott, {Andrew W} and Scheidt, {Karl A}",

year = "2009",

doi = "10.1021/ol802448c",

language = "English",

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pages = "105--108",

journal = "Organic Letters",

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T1 - NHC-Catalyzed Reactions of Aryloxyacetaldehydes: A Domino Elimination/Conjugate Addition/Acylation Process for the Synthesis of Substituted Coumarins

AU - Phillips, Eric M

AU - Wadamoto, Manabu

AU - Roth, Howard S

AU - Ott, Andrew W

AU - Scheidt, Karl A

PY - 2009

Y1 - 2009

N2 - N-Heterocyclic carbenes (NHCs) catalyze a domino Michael addition/acylation reaction to form 3,4-dihydrocoumarins. The reaction proceeds through addition of the NHC to an aryloxyaldehyde followed by elimination of a phenoxide leaving group, generating an enol intermediate. This transient nucleophile generated in situ performs a 1,4-addition onto a conjugate acceptor, and the carbene catalyst is regenerated upon acylation of the phenoxide anion resulting in formation of 3,4-dihydrocoumarins.

AB - N-Heterocyclic carbenes (NHCs) catalyze a domino Michael addition/acylation reaction to form 3,4-dihydrocoumarins. The reaction proceeds through addition of the NHC to an aryloxyaldehyde followed by elimination of a phenoxide leaving group, generating an enol intermediate. This transient nucleophile generated in situ performs a 1,4-addition onto a conjugate acceptor, and the carbene catalyst is regenerated upon acylation of the phenoxide anion resulting in formation of 3,4-dihydrocoumarins.

U2 - 10.1021/ol802448c

DO - 10.1021/ol802448c

M3 - Article

C2 - 19049403

SN - 1523-7060

VL - 11

SP - 105

EP - 108

JO - Organic Letters

JF - Organic Letters

ER -

NHC-Catalyzed Reactions of Aryloxyacetaldehydes: A Domino Elimination/Conjugate Addition/Acylation Process for the Synthesis of Substituted Coumarins

Abstract

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