Diastereoselective protonation of extended pyrrol-3-en-2-one enolates: An attempted 'de-epimerisation'

Jonathan Clayden; Rachel Turnbull; Ivan Pinto

doi:10.1016/j.tetasy.2005.05.042

Diastereoselective protonation of extended pyrrol-3-en-2-one enolates: An attempted 'de-epimerisation'

Jonathan Clayden^*, Rachel Turnbull, Ivan Pinto

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

24 Citations (Scopus)

Abstract

The extended cyclic enolate derived from a simple pyrrol-3-en-2-one (butenolactam) was deuterated at the 5-position with very high diastereoselectivity if the nitrogen atom carries an α-methyl-p- methoxybenzyl group. A similar diastereoselective protonation was observed in a pyrrol-3-en-2-one formed by dearomatising cyclisation of a pyrrole. Protonation of an N-α-methyl-p-methoxybenzyl dihydroisoindolone lacked stereoselectivity.

Original language	English
Pages (from-to)	2235-2241
Number of pages	7
Journal	Tetrahedron: Asymmetry
Volume	16
Issue number	13
DOIs	https://doi.org/10.1016/j.tetasy.2005.05.042
Publication status	Published - 4 Jul 2005

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title = "Diastereoselective protonation of extended pyrrol-3-en-2-one enolates: An attempted 'de-epimerisation'",

abstract = "The extended cyclic enolate derived from a simple pyrrol-3-en-2-one (butenolactam) was deuterated at the 5-position with very high diastereoselectivity if the nitrogen atom carries an α-methyl-p- methoxybenzyl group. A similar diastereoselective protonation was observed in a pyrrol-3-en-2-one formed by dearomatising cyclisation of a pyrrole. Protonation of an N-α-methyl-p-methoxybenzyl dihydroisoindolone lacked stereoselectivity.",

author = "Jonathan Clayden and Rachel Turnbull and Ivan Pinto",

year = "2005",

month = jul,

day = "4",

doi = "10.1016/j.tetasy.2005.05.042",

language = "English",

volume = "16",

pages = "2235--2241",

journal = "Tetrahedron: Asymmetry",

issn = "0957-4166",

publisher = "Elsevier",

number = "13",

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TY - JOUR

T1 - Diastereoselective protonation of extended pyrrol-3-en-2-one enolates

T2 - An attempted 'de-epimerisation'

AU - Clayden, Jonathan

AU - Turnbull, Rachel

AU - Pinto, Ivan

PY - 2005/7/4

Y1 - 2005/7/4

N2 - The extended cyclic enolate derived from a simple pyrrol-3-en-2-one (butenolactam) was deuterated at the 5-position with very high diastereoselectivity if the nitrogen atom carries an α-methyl-p- methoxybenzyl group. A similar diastereoselective protonation was observed in a pyrrol-3-en-2-one formed by dearomatising cyclisation of a pyrrole. Protonation of an N-α-methyl-p-methoxybenzyl dihydroisoindolone lacked stereoselectivity.

AB - The extended cyclic enolate derived from a simple pyrrol-3-en-2-one (butenolactam) was deuterated at the 5-position with very high diastereoselectivity if the nitrogen atom carries an α-methyl-p- methoxybenzyl group. A similar diastereoselective protonation was observed in a pyrrol-3-en-2-one formed by dearomatising cyclisation of a pyrrole. Protonation of an N-α-methyl-p-methoxybenzyl dihydroisoindolone lacked stereoselectivity.

UR - http://www.scopus.com/inward/record.url?scp=22044458497&partnerID=8YFLogxK

U2 - 10.1016/j.tetasy.2005.05.042

DO - 10.1016/j.tetasy.2005.05.042

M3 - Article (Academic Journal)

AN - SCOPUS:22044458497

SN - 0957-4166

VL - 16

SP - 2235

EP - 2241

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

IS - 13

ER -

Diastereoselective protonation of extended pyrrol-3-en-2-one enolates: An attempted 'de-epimerisation'

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