An Expedient Synthesis of N-Acceptor-Substituted 2,3-Dihydropyrrols from the Corresponding 2-Pyrrolidinones

Thorsten Bach; Harm Brummerhop

An Expedient Synthesis of N-Acceptor-Substituted 2,3-Dihydropyrrols from the Corresponding 2-Pyrrolidinones

Thorsten Bach
, Harm Brummerhop

Philipps-Universität Marburg

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

8 Scopus citations

Abstract

The title compounds 1 were prepared from the corresponding N-acceptor substituted 2-methoxypyrrolidines 3 by elimination with trimethylsilyl trifluoromethanesulfonate (TMSOTf) and N,N-di-iso-propyl ethyl amine (6 exampies, 57-84% yield). The enantiomerically pure N-methoxy-carbonyl protected elimination substrates 3aa and 3ab were synthesized from the L-pyroglutamic acid derived pyrrolidinones 6a and 6b in three steps (80-83% yield overall).

Original language	English
Pages (from-to)	312-315
Number of pages	4
Journal	Advanced Synthesis and Catalysis
Volume	341
Issue number	3
State	Published - 1999
Externally published	Yes

Keywords

Dihydropyrrols
Eliminations
Nitrogen heterocycles
Reductions
Synthetic methods

Cite this

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title = "An Expedient Synthesis of N-Acceptor-Substituted 2,3-Dihydropyrrols from the Corresponding 2-Pyrrolidinones",

abstract = "The title compounds 1 were prepared from the corresponding N-acceptor substituted 2-methoxypyrrolidines 3 by elimination with trimethylsilyl trifluoromethanesulfonate (TMSOTf) and N,N-di-iso-propyl ethyl amine (6 exampies, 57-84\% yield). The enantiomerically pure N-methoxy-carbonyl protected elimination substrates 3aa and 3ab were synthesized from the L-pyroglutamic acid derived pyrrolidinones 6a and 6b in three steps (80-83\% yield overall).",

keywords = "Dihydropyrrols, Eliminations, Nitrogen heterocycles, Reductions, Synthetic methods",

author = "Thorsten Bach and Harm Brummerhop",

year = "1999",

language = "English",

volume = "341",

pages = "312--315",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

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TY - JOUR

T1 - An Expedient Synthesis of N-Acceptor-Substituted 2,3-Dihydropyrrols from the Corresponding 2-Pyrrolidinones

AU - Bach, Thorsten

AU - Brummerhop, Harm

PY - 1999

Y1 - 1999

N2 - The title compounds 1 were prepared from the corresponding N-acceptor substituted 2-methoxypyrrolidines 3 by elimination with trimethylsilyl trifluoromethanesulfonate (TMSOTf) and N,N-di-iso-propyl ethyl amine (6 exampies, 57-84% yield). The enantiomerically pure N-methoxy-carbonyl protected elimination substrates 3aa and 3ab were synthesized from the L-pyroglutamic acid derived pyrrolidinones 6a and 6b in three steps (80-83% yield overall).

AB - The title compounds 1 were prepared from the corresponding N-acceptor substituted 2-methoxypyrrolidines 3 by elimination with trimethylsilyl trifluoromethanesulfonate (TMSOTf) and N,N-di-iso-propyl ethyl amine (6 exampies, 57-84% yield). The enantiomerically pure N-methoxy-carbonyl protected elimination substrates 3aa and 3ab were synthesized from the L-pyroglutamic acid derived pyrrolidinones 6a and 6b in three steps (80-83% yield overall).

KW - Dihydropyrrols

KW - Eliminations

KW - Nitrogen heterocycles

KW - Reductions

KW - Synthetic methods

UR - https://www.scopus.com/pages/publications/0347710676

M3 - Article

AN - SCOPUS:0347710676

SN - 1615-4150

VL - 341

SP - 312

EP - 315

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 3

ER -

An Expedient Synthesis of N-Acceptor-Substituted 2,3-Dihydropyrrols from the Corresponding 2-Pyrrolidinones

Abstract

Keywords

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