A HIGHLY EFFICIENT FREE-RADICAL APPROACH TO TRISUBSTITUTED PYRROLIDINONES

A F  PARSONS; J K  TAYLOR

A HIGHLY EFFICIENT FREE-RADICAL APPROACH TO TRISUBSTITUTED PYRROLIDINONES

Chemistry

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

Abstract

The radical-mediated cyclisation of serine derived alpha-chloroamides has beer found to be influenced in both yield and stereoselectivity by the nature of the substituent at the site of radical generation-radicals substituted at the alpha-position by methyl, phenyl and dichloro groups underwent smooth cyclisation to give excellent yield of pyrrolidinones in which the trans-C-2 : C-3 isomer predominated-this procedure has potential application to a new synthesis of the kainoid amino acids.

Original language	English
Pages (from-to)	1224-1225
Number of pages	2
Journal	JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS
Issue number	15
Publication status	Published - 7 Aug 1993

Keywords

ACROMELIC ACID
AMINO-ACIDS
ENANTIOSELECTIVE SYNTHESIS
CLITOCYBE-ACROMELALGA
MEDIATED CYCLIZATION
5-MEMBERED LACTAMS
DOMOIC ACID
ROUTE

Cite this

@article{e9a93e6afc48424097da8c4fcda905ff,

title = "A HIGHLY EFFICIENT FREE-RADICAL APPROACH TO TRISUBSTITUTED PYRROLIDINONES",

abstract = "The radical-mediated cyclisation of serine derived alpha-chloroamides has beer found to be influenced in both yield and stereoselectivity by the nature of the substituent at the site of radical generation-radicals substituted at the alpha-position by methyl, phenyl and dichloro groups underwent smooth cyclisation to give excellent yield of pyrrolidinones in which the trans-C-2 : C-3 isomer predominated-this procedure has potential application to a new synthesis of the kainoid amino acids.",

keywords = "ACROMELIC ACID, AMINO-ACIDS, ENANTIOSELECTIVE SYNTHESIS, CLITOCYBE-ACROMELALGA, MEDIATED CYCLIZATION, 5-MEMBERED LACTAMS, DOMOIC ACID, ROUTE",

author = "PARSONS, {A F} and TAYLOR, {J K}",

year = "1993",

month = aug,

day = "7",

language = "English",

pages = "1224--1225",

journal = "JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS",

issn = "0022-4936",

publisher = "Chemical Society",

number = "15",

}

TY - JOUR

T1 - A HIGHLY EFFICIENT FREE-RADICAL APPROACH TO TRISUBSTITUTED PYRROLIDINONES

AU - PARSONS, A F

AU - TAYLOR, J K

PY - 1993/8/7

Y1 - 1993/8/7

N2 - The radical-mediated cyclisation of serine derived alpha-chloroamides has beer found to be influenced in both yield and stereoselectivity by the nature of the substituent at the site of radical generation-radicals substituted at the alpha-position by methyl, phenyl and dichloro groups underwent smooth cyclisation to give excellent yield of pyrrolidinones in which the trans-C-2 : C-3 isomer predominated-this procedure has potential application to a new synthesis of the kainoid amino acids.

AB - The radical-mediated cyclisation of serine derived alpha-chloroamides has beer found to be influenced in both yield and stereoselectivity by the nature of the substituent at the site of radical generation-radicals substituted at the alpha-position by methyl, phenyl and dichloro groups underwent smooth cyclisation to give excellent yield of pyrrolidinones in which the trans-C-2 : C-3 isomer predominated-this procedure has potential application to a new synthesis of the kainoid amino acids.

KW - ACROMELIC ACID

KW - AMINO-ACIDS

KW - ENANTIOSELECTIVE SYNTHESIS

KW - CLITOCYBE-ACROMELALGA

KW - MEDIATED CYCLIZATION

KW - 5-MEMBERED LACTAMS

KW - DOMOIC ACID

KW - ROUTE

M3 - Article

SN - 0022-4936

SP - 1224

EP - 1225

JO - JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS

JF - JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS

IS - 15

ER -