Stereoselective synthesis, NMR conformational study and Diels-Alder reaction of β-functionalized 1-acetylvinyl arenecarboxylates

Javier Peralta; Joseph P. Bullock; Roderick W. Bates; Simon Bott; Gerardo Zepeda; Joaquín Tamariz

doi:10.1016/0040-4020(95)00140-4

Stereoselective synthesis, NMR conformational study and Diels-Alder reaction of β-functionalized 1-acetylvinyl arenecarboxylates

Javier Peralta^*, Joseph P. Bullock, Roderick W. Bates, Simon Bott, Gerardo Zepeda, Joaquín Tamariz

^*Corresponding author for this work

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

21 Citations (Scopus)

Abstract

A stereoselective synthesis of novel β-substituted 1-acetylvinyl arenecarboxylates 2a-2h, via the bromo derivative 4a, is described. Isomer Z was the only product formed. Low temperature NMR experiments showed an s-cis/s-trans (20:80) conformeric equilibrium, and also a restricted rotational C-N barrier in 2a. X-ray diffraction of the latter revealed a planar s-trans conformation. Alkene 4a proved to be more reactive than 2a-2h towards cyclopentadiene (6) and isoprene (11) in Diels-Alder additions, giving the corresponding adducts 10 and 14 in high stereo- and regioselectivity.

Original language	English
Pages (from-to)	3979-3996
Number of pages	18
Journal	Tetrahedron
Volume	51
Issue number	14
DOIs	https://doi.org/10.1016/0040-4020(95)00140-4
Publication status	Published - Apr 3 1995
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/0040-4020(95)00140-4

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title = "Stereoselective synthesis, NMR conformational study and Diels-Alder reaction of β-functionalized 1-acetylvinyl arenecarboxylates",

abstract = "A stereoselective synthesis of novel β-substituted 1-acetylvinyl arenecarboxylates 2a-2h, via the bromo derivative 4a, is described. Isomer Z was the only product formed. Low temperature NMR experiments showed an s-cis/s-trans (20:80) conformeric equilibrium, and also a restricted rotational C-N barrier in 2a. X-ray diffraction of the latter revealed a planar s-trans conformation. Alkene 4a proved to be more reactive than 2a-2h towards cyclopentadiene (6) and isoprene (11) in Diels-Alder additions, giving the corresponding adducts 10 and 14 in high stereo- and regioselectivity.",

author = "Javier Peralta and Bullock, {Joseph P.} and Bates, {Roderick W.} and Simon Bott and Gerardo Zepeda and Joaqu{\'i}n Tamariz",

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T1 - Stereoselective synthesis, NMR conformational study and Diels-Alder reaction of β-functionalized 1-acetylvinyl arenecarboxylates

AU - Peralta, Javier

AU - Bullock, Joseph P.

AU - Bates, Roderick W.

AU - Bott, Simon

AU - Zepeda, Gerardo

AU - Tamariz, Joaquín

PY - 1995/4/3

Y1 - 1995/4/3

N2 - A stereoselective synthesis of novel β-substituted 1-acetylvinyl arenecarboxylates 2a-2h, via the bromo derivative 4a, is described. Isomer Z was the only product formed. Low temperature NMR experiments showed an s-cis/s-trans (20:80) conformeric equilibrium, and also a restricted rotational C-N barrier in 2a. X-ray diffraction of the latter revealed a planar s-trans conformation. Alkene 4a proved to be more reactive than 2a-2h towards cyclopentadiene (6) and isoprene (11) in Diels-Alder additions, giving the corresponding adducts 10 and 14 in high stereo- and regioselectivity.

AB - A stereoselective synthesis of novel β-substituted 1-acetylvinyl arenecarboxylates 2a-2h, via the bromo derivative 4a, is described. Isomer Z was the only product formed. Low temperature NMR experiments showed an s-cis/s-trans (20:80) conformeric equilibrium, and also a restricted rotational C-N barrier in 2a. X-ray diffraction of the latter revealed a planar s-trans conformation. Alkene 4a proved to be more reactive than 2a-2h towards cyclopentadiene (6) and isoprene (11) in Diels-Alder additions, giving the corresponding adducts 10 and 14 in high stereo- and regioselectivity.

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JF - Tetrahedron

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ER -

Stereoselective synthesis, NMR conformational study and Diels-Alder reaction of β-functionalized 1-acetylvinyl arenecarboxylates

Abstract

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