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

Escuela Nacional de Ciencias Biológicas (ENCB)

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

19 Scopus citations

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
State	Published - 3 Apr 1995

Access to Document

10.1016/0040-4020(95)00140-4

Cite this

@article{537e172830e64f54a51927d36979152a,

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",

year = "1995",

month = apr,

day = "3",

doi = "10.1016/0040-4020(95)00140-4",

language = "Ingl{\'e}s",

volume = "51",

pages = "3979--3996",

journal = "Tetrahedron",

issn = "0040-4020",

number = "14",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=0028964197&partnerID=8YFLogxK

U2 - 10.1016/0040-4020(95)00140-4

DO - 10.1016/0040-4020(95)00140-4

M3 - Artículo

SN - 0040-4020

VL - 51

SP - 3979

EP - 3996

JO - Tetrahedron

JF - Tetrahedron

IS - 14

ER -

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

Abstract

Access to Document

Other files and links

Fingerprint

Cite this