Tributyltin hydride-mediated radical cyclisation of aldehydes and unsaturated ketones: the synthesis of hydroxy tetrahydrofurans, chromanols and related compounds

D  Bebbington; J  Bentley; P A  Nilsson; A F  Parsons

Tributyltin hydride-mediated radical cyclisation of aldehydes and unsaturated ketones: the synthesis of hydroxy tetrahydrofurans, chromanols and related compounds

D Bebbington, J Bentley, P A Nilsson, A F Parsons

Chemistry

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

Abstract

The tributyltin hydride-mediated cyclisation of unsaturated ethers bearing an aldehyde or alpha,beta -unsaturated ketone group is reported. Cyclisation proceeds via addition of the tributyltin radical to the carbonyl double bond and the resultant O-stannyl ketyl can add intramolecularly to electron-rich double bonds to form hydroxy tetrahydrofurans, chromanols or related compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	8941-8945
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	46
Publication status	Published - 11 Nov 2000

Keywords

cyclisation
oxygen heterocycles
radicals and radical reactions
tin and compounds
O-STANNYL KETYLS
CYCLIZATION REACTIONS
RING-CLOSURE
PYRROLIDINES
PIPERIDINES
AMIDES
ESTERS

Cite this

@article{7daea50e1cbe45d280a2ff1ca0c7dae0,

title = "Tributyltin hydride-mediated radical cyclisation of aldehydes and unsaturated ketones: the synthesis of hydroxy tetrahydrofurans, chromanols and related compounds",

abstract = "The tributyltin hydride-mediated cyclisation of unsaturated ethers bearing an aldehyde or alpha,beta -unsaturated ketone group is reported. Cyclisation proceeds via addition of the tributyltin radical to the carbonyl double bond and the resultant O-stannyl ketyl can add intramolecularly to electron-rich double bonds to form hydroxy tetrahydrofurans, chromanols or related compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.",

keywords = "cyclisation, oxygen heterocycles, radicals and radical reactions, tin and compounds, O-STANNYL KETYLS, CYCLIZATION REACTIONS, RING-CLOSURE, PYRROLIDINES, PIPERIDINES, AMIDES, ESTERS",

author = "D Bebbington and J Bentley and Nilsson, {P A} and Parsons, {A F}",

year = "2000",

month = nov,

day = "11",

language = "English",

volume = "41",

pages = "8941--8945",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "46",

}

TY - JOUR

T1 - Tributyltin hydride-mediated radical cyclisation of aldehydes and unsaturated ketones: the synthesis of hydroxy tetrahydrofurans, chromanols and related compounds

AU - Bebbington, D

AU - Bentley, J

AU - Nilsson, P A

AU - Parsons, A F

PY - 2000/11/11

Y1 - 2000/11/11

N2 - The tributyltin hydride-mediated cyclisation of unsaturated ethers bearing an aldehyde or alpha,beta -unsaturated ketone group is reported. Cyclisation proceeds via addition of the tributyltin radical to the carbonyl double bond and the resultant O-stannyl ketyl can add intramolecularly to electron-rich double bonds to form hydroxy tetrahydrofurans, chromanols or related compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

AB - The tributyltin hydride-mediated cyclisation of unsaturated ethers bearing an aldehyde or alpha,beta -unsaturated ketone group is reported. Cyclisation proceeds via addition of the tributyltin radical to the carbonyl double bond and the resultant O-stannyl ketyl can add intramolecularly to electron-rich double bonds to form hydroxy tetrahydrofurans, chromanols or related compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

KW - cyclisation

KW - oxygen heterocycles

KW - radicals and radical reactions

KW - tin and compounds

KW - O-STANNYL KETYLS

KW - CYCLIZATION REACTIONS

KW - RING-CLOSURE

KW - PYRROLIDINES

KW - PIPERIDINES

KW - AMIDES

KW - ESTERS

M3 - Article

SN - 0040-4039

VL - 41

SP - 8941

EP - 8945

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 46

ER -