Intramolecular Diels-Alder cycloaddition of N-allyl-N-(2-furylmethyl)amides - First step of a new route towards the synthesis of a densely functionalized pyrrolizidine ring

F  Ghelfi; A F  Parsons; D  Tommasini; A  Mucci

Intramolecular Diels-Alder cycloaddition of N-allyl-N-(2-furylmethyl)amides - First step of a new route towards the synthesis of a densely functionalized pyrrolizidine ring

F Ghelfi, A F Parsons, D Tommasini, A Mucci

Chemistry

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

Abstract

The intramolecular Diels-Alder reaction of N-allyl-N-(2-furylmethyl)amides to exo-N-acyl-3-aza-10-oxatricyclo[5.2.1.0(1)-,5]dec-8-enes is described. The cycloaddition is controlled not only by the size of the amide appendage, but, also by electronegativity of the amide. An example of a new approach towards the synthesis of a highly functionalized pyrrolizidine ring, which links this Diels-Alder cycloaddition to an halogen atom transfer radical cyclization, is reported.

Original language	English
Pages (from-to)	1845-1852
Number of pages	8
Journal	European Journal of Organic Chemistry
Issue number	10
Publication status	Published - May 2001

Keywords

amides
Diels-Alder reactions
polycyclic aliphatic compounds
pyrrolizidines
radicals
radical reactions
TRICYCLIC NITROGEN-HETEROCYCLES
RADICAL CYCLIZATION
GAMMA-LACTAMS
FURAN DIENE
ORGANOMETALLIC REAGENTS
CONSTRUCTION
IMDAF
REARRANGEMENT
SUBSTITUENTS
DERIVATIVES

Cite this

@article{79ea327fa82a4503afacac09e8a5937f,

title = "Intramolecular Diels-Alder cycloaddition of N-allyl-N-(2-furylmethyl)amides - First step of a new route towards the synthesis of a densely functionalized pyrrolizidine ring",

abstract = "The intramolecular Diels-Alder reaction of N-allyl-N-(2-furylmethyl)amides to exo-N-acyl-3-aza-10-oxatricyclo[5.2.1.0(1)-,5]dec-8-enes is described. The cycloaddition is controlled not only by the size of the amide appendage, but, also by electronegativity of the amide. An example of a new approach towards the synthesis of a highly functionalized pyrrolizidine ring, which links this Diels-Alder cycloaddition to an halogen atom transfer radical cyclization, is reported.",

keywords = "amides, Diels-Alder reactions, polycyclic aliphatic compounds, pyrrolizidines, radicals, radical reactions, TRICYCLIC NITROGEN-HETEROCYCLES, RADICAL CYCLIZATION, GAMMA-LACTAMS, FURAN DIENE, ORGANOMETALLIC REAGENTS, CONSTRUCTION, IMDAF, REARRANGEMENT, SUBSTITUENTS, DERIVATIVES",

author = "F Ghelfi and Parsons, {A F} and D Tommasini and A Mucci",

year = "2001",

month = may,

language = "English",

pages = "1845--1852",

journal = "European Journal of Organic Chemistry",

issn = "1099-0690",

publisher = "Wiley-Blackwell",

number = "10",

}

TY - JOUR

T1 - Intramolecular Diels-Alder cycloaddition of N-allyl-N-(2-furylmethyl)amides - First step of a new route towards the synthesis of a densely functionalized pyrrolizidine ring

AU - Ghelfi, F

AU - Parsons, A F

AU - Tommasini, D

AU - Mucci, A

PY - 2001/5

Y1 - 2001/5

N2 - The intramolecular Diels-Alder reaction of N-allyl-N-(2-furylmethyl)amides to exo-N-acyl-3-aza-10-oxatricyclo[5.2.1.0(1)-,5]dec-8-enes is described. The cycloaddition is controlled not only by the size of the amide appendage, but, also by electronegativity of the amide. An example of a new approach towards the synthesis of a highly functionalized pyrrolizidine ring, which links this Diels-Alder cycloaddition to an halogen atom transfer radical cyclization, is reported.

AB - The intramolecular Diels-Alder reaction of N-allyl-N-(2-furylmethyl)amides to exo-N-acyl-3-aza-10-oxatricyclo[5.2.1.0(1)-,5]dec-8-enes is described. The cycloaddition is controlled not only by the size of the amide appendage, but, also by electronegativity of the amide. An example of a new approach towards the synthesis of a highly functionalized pyrrolizidine ring, which links this Diels-Alder cycloaddition to an halogen atom transfer radical cyclization, is reported.

KW - amides

KW - Diels-Alder reactions

KW - polycyclic aliphatic compounds

KW - pyrrolizidines

KW - radicals

KW - radical reactions

KW - TRICYCLIC NITROGEN-HETEROCYCLES

KW - RADICAL CYCLIZATION

KW - GAMMA-LACTAMS

KW - FURAN DIENE

KW - ORGANOMETALLIC REAGENTS

KW - CONSTRUCTION

KW - IMDAF

KW - REARRANGEMENT

KW - SUBSTITUENTS

KW - DERIVATIVES

M3 - Article

SN - 1099-0690

SP - 1845

EP - 1852

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 10

ER -