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

Giada Arena; C 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, C Chun Chen, Daniele Leonori, Varinder K Aggarwal

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

Abstract

3-Methyl vinyl aziridine undergoes a mild MgI2-promoted SN2′ 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	3
Journal	Organic Letters
Volume	15
Issue number	16
DOIs	https://doi.org/10.1021/ol4020333
Publication status	Published - 2 Aug 2013

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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 SN2′ 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.",

author = "Giada Arena and Chen, {C Chun} and Daniele Leonori and Aggarwal, {Varinder K}",

year = "2013",

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journal = "Organic Letters",

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

AU - Arena, Giada

AU - Chen, C Chun

AU - Leonori, Daniele

AU - Aggarwal, Varinder K

PY - 2013/8/2

Y1 - 2013/8/2

N2 - 3-Methyl vinyl aziridine undergoes a mild MgI2-promoted SN2′ 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 SN2′ 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.

U2 - 10.1021/ol4020333

DO - 10.1021/ol4020333

M3 - Article

SN - 1523-7052

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

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