First organophosphorus radical-mediated cyclisations to afford medium-sized rings: eight-membered lactones and seven- and eight-membered lactams

S  Lang; Michael James Corr; N  Muir; T A  Khan; F  Schonebeck; J A  Murphy; A H  Payne; A C  Williams

doi:10.1016/j.tetlet.2005.04.032

First organophosphorus radical-mediated cyclisations to afford medium-sized rings: eight-membered lactones and seven- and eight-membered lactams

S Lang, Michael James Corr, N Muir, T A Khan, F Schonebeck, J A Murphy, A H Payne, A C Williams

School of Chemistry

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

Abstract

The phosphorus based radical precursors N-ethylpiperidine hypophosphite (EPHP) and diethylphosphine oxide (DEPO) are efficient reagents for carrying out the formation of seven- and eight-membered rings. Esters and amides were successfully converted into the corresponding eight-membered lactones and seven- and eight-membered lactams in good to excellent yields. (c) 2005 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	4027-4030
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	23
DOIs	https://doi.org/10.1016/j.tetlet.2005.04.032
Publication status	Published - 6 Jun 2005

Keywords

radical
phosphorus
DEPO
EPHP
cyclisation
KETYL-OLEFIN CYCLIZATION
CARBON BOND FORMATION
(ALKOXYCARBONYL)METHYL RADICALS
STEREOSELECTIVE-SYNTHESIS
8-ENDO CYCLIZATION
EFFICIENT ROUTE
AQUEOUS-MEDIA
HYPOPHOSPHITE
WATER
ESTERS

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10.1016/j.tetlet.2005.04.032

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title = "First organophosphorus radical-mediated cyclisations to afford medium-sized rings: eight-membered lactones and seven- and eight-membered lactams",

abstract = "The phosphorus based radical precursors N-ethylpiperidine hypophosphite (EPHP) and diethylphosphine oxide (DEPO) are efficient reagents for carrying out the formation of seven- and eight-membered rings. Esters and amides were successfully converted into the corresponding eight-membered lactones and seven- and eight-membered lactams in good to excellent yields. (c) 2005 Elsevier Ltd. All rights reserved.",

keywords = "radical, phosphorus, DEPO, EPHP, cyclisation, KETYL-OLEFIN CYCLIZATION, CARBON BOND FORMATION, (ALKOXYCARBONYL)METHYL RADICALS, STEREOSELECTIVE-SYNTHESIS, 8-ENDO CYCLIZATION, EFFICIENT ROUTE, AQUEOUS-MEDIA, HYPOPHOSPHITE, WATER, ESTERS",

author = "S Lang and Corr, \{Michael James\} and N Muir and Khan, \{T A\} and F Schonebeck and Murphy, \{J A\} and Payne, \{A H\} and Williams, \{A C\}",

year = "2005",

month = jun,

day = "6",

doi = "10.1016/j.tetlet.2005.04.032",

language = "English",

volume = "46",

pages = "4027--4030",

journal = "Tetrahedron Letters",

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number = "23",

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TY - JOUR

T1 - First organophosphorus radical-mediated cyclisations to afford medium-sized rings: eight-membered lactones and seven- and eight-membered lactams

AU - Lang, S

AU - Corr, Michael James

AU - Muir, N

AU - Khan, T A

AU - Schonebeck, F

AU - Murphy, J A

AU - Payne, A H

AU - Williams, A C

PY - 2005/6/6

Y1 - 2005/6/6

N2 - The phosphorus based radical precursors N-ethylpiperidine hypophosphite (EPHP) and diethylphosphine oxide (DEPO) are efficient reagents for carrying out the formation of seven- and eight-membered rings. Esters and amides were successfully converted into the corresponding eight-membered lactones and seven- and eight-membered lactams in good to excellent yields. (c) 2005 Elsevier Ltd. All rights reserved.

AB - The phosphorus based radical precursors N-ethylpiperidine hypophosphite (EPHP) and diethylphosphine oxide (DEPO) are efficient reagents for carrying out the formation of seven- and eight-membered rings. Esters and amides were successfully converted into the corresponding eight-membered lactones and seven- and eight-membered lactams in good to excellent yields. (c) 2005 Elsevier Ltd. All rights reserved.

KW - radical

KW - phosphorus

KW - DEPO

KW - EPHP

KW - cyclisation

KW - KETYL-OLEFIN CYCLIZATION

KW - CARBON BOND FORMATION

KW - (ALKOXYCARBONYL)METHYL RADICALS

KW - STEREOSELECTIVE-SYNTHESIS

KW - 8-ENDO CYCLIZATION

KW - EFFICIENT ROUTE

KW - AQUEOUS-MEDIA

KW - HYPOPHOSPHITE

KW - WATER

KW - ESTERS

UR - https://www.scopus.com/pages/publications/18844424348

U2 - 10.1016/j.tetlet.2005.04.032

DO - 10.1016/j.tetlet.2005.04.032

M3 - Article

SN - 0040-4039

VL - 46

SP - 4027

EP - 4030

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 23

ER -

First organophosphorus radical-mediated cyclisations to afford medium-sized rings: eight-membered lactones and seven- and eight-membered lactams

Abstract

Keywords

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