Concise Synthesis of (+)-allo-Kainic Acid via MgI2-Mediated Tandem Aziridine Ring Opening-Formal [3+2] Cycloaddition

Giada Arena; Chia-Chun Chen; Daniele Leonori; Varinder K. Aggarwal

doi:10.1021/ol4020333

Concise Synthesis of (+)-allo-Kainic Acid via MgI2-Mediated Tandem Aziridine Ring Opening-Formal [3+2] Cycloaddition

Giada Arena
, Chia-Chun Chen
, Daniele Leonori^*
, Varinder K. Aggarwal

^*Corresponding author for this work

School of Chemistry

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

49 Citations (Scopus)

634 Downloads (Pure)

Abstract

3-Methyl vinyl aziridine undergoes a mild MgI2-promoted S(N)2' ring opening and concomitant cyclization with fumarate Michael acceptors to give trisubstituted pyrrolidines. The process is efficient and highly diastereoselective. This methodology has been applied to a concise asymmetric synthesis of (+)-allo-kainic acid.

Original language	English
Pages (from-to)	4250-4253
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	16
Early online date	2 Aug 2013
DOIs	https://doi.org/10.1021/ol4020333
Publication status	Published - 16 Aug 2013

Research Groups and Themes

Organic & Biological

Keywords

CHIRAL NITRIDOMANGANESE COMPLEX
HIGHLY SUBSTITUTED PYRROLIDINES
CATALYZED CASCADE REACTIONS
EXCITATORY AMINO-ACIDS
ENE-TYPE REACTIONS
ACTIVATED OLEFINS
ENANTIOSELECTIVE SYNTHESIS
ASYMMETRIC-SYNTHESIS
KAINIC ACID
(+/-)-ALPHA-ALLOKAINIC ACID

Access to Document

10.1021/ol4020333

G Arena Org Lett 2013
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright 2013 © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/page/policy/articlesonrequest/index.html.
Accepted author manuscript, 535 KB

http://pubs.acs.org/doi/abs/10.1021/ol4020333

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3-month Core Capability for Chemistry Research
Crosby, J. (Principal Investigator)
1/01/13 → 1/04/13
Project: Research
Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis
Aggarwal, V. K. (Principal Investigator)
14/05/12 → 13/01/18
Project: Research
GENERAL AND CONVERGENT STRATEGY FOR ASYMMETRIC SYNTHESIS
Aggarwal, V. K. (Principal Investigator)
1/10/07 → 1/04/13
Project: Research

Cite this

@article{4d411fce4fee4f13b9a9c1a997121c4c,

title = "Concise Synthesis of (+)-allo-Kainic Acid via MgI2-Mediated Tandem Aziridine Ring Opening-Formal [3+2] Cycloaddition",

abstract = "3-Methyl vinyl aziridine undergoes a mild MgI2-promoted S(N)2' ring opening and concomitant cyclization with fumarate Michael acceptors to give trisubstituted pyrrolidines. The process is efficient and highly diastereoselective. This methodology has been applied to a concise asymmetric synthesis of (+)-allo-kainic acid.",

keywords = "CHIRAL NITRIDOMANGANESE COMPLEX, HIGHLY SUBSTITUTED PYRROLIDINES, CATALYZED CASCADE REACTIONS, EXCITATORY AMINO-ACIDS, ENE-TYPE REACTIONS, ACTIVATED OLEFINS, ENANTIOSELECTIVE SYNTHESIS, ASYMMETRIC-SYNTHESIS, KAINIC ACID, (+/-)-ALPHA-ALLOKAINIC ACID",

author = "Giada Arena and Chia-Chun Chen and Daniele Leonori and Aggarwal, \{Varinder K.\}",

year = "2013",

month = aug,

day = "16",

doi = "10.1021/ol4020333",

language = "English",

volume = "15",

pages = "4250--4253",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "16",

}

TY - JOUR

T1 - Concise Synthesis of (+)-allo-Kainic Acid via MgI2-Mediated Tandem Aziridine Ring Opening-Formal [3+2] Cycloaddition

AU - Arena, Giada

AU - Chen, Chia-Chun

AU - Leonori, Daniele

AU - Aggarwal, Varinder K.

PY - 2013/8/16

Y1 - 2013/8/16

N2 - 3-Methyl vinyl aziridine undergoes a mild MgI2-promoted S(N)2' ring opening and concomitant cyclization with fumarate Michael acceptors to give trisubstituted pyrrolidines. The process is efficient and highly diastereoselective. This methodology has been applied to a concise asymmetric synthesis of (+)-allo-kainic acid.

AB - 3-Methyl vinyl aziridine undergoes a mild MgI2-promoted S(N)2' ring opening and concomitant cyclization with fumarate Michael acceptors to give trisubstituted pyrrolidines. The process is efficient and highly diastereoselective. This methodology has been applied to a concise asymmetric synthesis of (+)-allo-kainic acid.

KW - CHIRAL NITRIDOMANGANESE COMPLEX

KW - HIGHLY SUBSTITUTED PYRROLIDINES

KW - CATALYZED CASCADE REACTIONS

KW - EXCITATORY AMINO-ACIDS

KW - ENE-TYPE REACTIONS

KW - ACTIVATED OLEFINS

KW - ENANTIOSELECTIVE SYNTHESIS

KW - ASYMMETRIC-SYNTHESIS

KW - KAINIC ACID

KW - (+/-)-ALPHA-ALLOKAINIC ACID

U2 - 10.1021/ol4020333

DO - 10.1021/ol4020333

M3 - Article (Academic Journal)

C2 - 23909824

SN - 1523-7060

VL - 15

SP - 4250

EP - 4253

JO - Organic Letters

JF - Organic Letters

IS - 16

ER -

Concise Synthesis of (+)-allo-Kainic Acid via MgI2-Mediated Tandem Aziridine Ring Opening-Formal [3+2] Cycloaddition

Abstract

Research Groups and Themes

Keywords

Access to Document

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Projects

3-month Core Capability for Chemistry Research

Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis

GENERAL AND CONVERGENT STRATEGY FOR ASYMMETRIC SYNTHESIS

Cite this