Tandem one-pot synthesis of α-(aminomethylene)-γ-butyrolactones via regioselective epoxide ring-opening with the Blaise reaction intermediate

Young Ok Ko; Yu Sung Chun; Youngmee Kim; Sung Jin Kim; Hyunik Shin; Sang Gi Lee

doi:10.1016/j.tetlet.2010.10.108

Tandem one-pot synthesis of α-(aminomethylene)-γ-butyrolactones via regioselective epoxide ring-opening with the Blaise reaction intermediate

Young Ok Ko, Yu Sung Chun, Youngmee Kim, Sung Jin Kim, Hyunik Shin, Sang Gi Lee

Department of Chemistry & Nanoscience

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

24 Scopus citations

Abstract

A novel tandem one-pot method for the synthesis of α-aminomethylene- γ-butyrolactone derivatives has been developed through the regioselective epoxide opening reactions with the Blaise reaction intermediates, generated by the reaction of a Reformatsky reagent with nitriles. Formation of a modified Blaise reaction intermediate by the addition of a stoichiometric amount of n-BuLi followed by slow addition of epoxide is required for the good yield of γ-butyrolactones.

Original language	English
Pages (from-to)	6893-6896
Number of pages	4
Journal	Tetrahedron Letters
Volume	51
Issue number	52
DOIs	https://doi.org/10.1016/j.tetlet.2010.10.108
State	Published - 29 Dec 2010

Bibliographical note

Funding Information:
This work was supported by the Korea Research Foundation ( KRF-20090070898 and KRF-20090063004 ), the Seoul R&D fellowship for Y. O. Ko, and RP-supporting from Ewha Womans University for Y. S. Chun.

Keywords

Blaise reaction intermediate
Butyrolactone
Epoxide opening
Regioselectivity
Tandem reaction

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10.1016/j.tetlet.2010.10.108

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title = "Tandem one-pot synthesis of α-(aminomethylene)-γ-butyrolactones via regioselective epoxide ring-opening with the Blaise reaction intermediate",

abstract = "A novel tandem one-pot method for the synthesis of α-aminomethylene- γ-butyrolactone derivatives has been developed through the regioselective epoxide opening reactions with the Blaise reaction intermediates, generated by the reaction of a Reformatsky reagent with nitriles. Formation of a modified Blaise reaction intermediate by the addition of a stoichiometric amount of n-BuLi followed by slow addition of epoxide is required for the good yield of γ-butyrolactones.",

keywords = "Blaise reaction intermediate, Butyrolactone, Epoxide opening, Regioselectivity, Tandem reaction",

author = "Ko, {Young Ok} and Chun, {Yu Sung} and Youngmee Kim and Kim, {Sung Jin} and Hyunik Shin and Lee, {Sang Gi}",

note = "Funding Information: This work was supported by the Korea Research Foundation ( KRF-20090070898 and KRF-20090063004 ), the Seoul R&D fellowship for Y. O. Ko, and RP-supporting from Ewha Womans University for Y. S. Chun. ",

year = "2010",

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doi = "10.1016/j.tetlet.2010.10.108",

language = "English",

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T1 - Tandem one-pot synthesis of α-(aminomethylene)-γ-butyrolactones via regioselective epoxide ring-opening with the Blaise reaction intermediate

AU - Ko, Young Ok

AU - Chun, Yu Sung

AU - Kim, Youngmee

AU - Kim, Sung Jin

AU - Shin, Hyunik

AU - Lee, Sang Gi

N1 - Funding Information: This work was supported by the Korea Research Foundation ( KRF-20090070898 and KRF-20090063004 ), the Seoul R&D fellowship for Y. O. Ko, and RP-supporting from Ewha Womans University for Y. S. Chun.

PY - 2010/12/29

Y1 - 2010/12/29

N2 - A novel tandem one-pot method for the synthesis of α-aminomethylene- γ-butyrolactone derivatives has been developed through the regioselective epoxide opening reactions with the Blaise reaction intermediates, generated by the reaction of a Reformatsky reagent with nitriles. Formation of a modified Blaise reaction intermediate by the addition of a stoichiometric amount of n-BuLi followed by slow addition of epoxide is required for the good yield of γ-butyrolactones.

AB - A novel tandem one-pot method for the synthesis of α-aminomethylene- γ-butyrolactone derivatives has been developed through the regioselective epoxide opening reactions with the Blaise reaction intermediates, generated by the reaction of a Reformatsky reagent with nitriles. Formation of a modified Blaise reaction intermediate by the addition of a stoichiometric amount of n-BuLi followed by slow addition of epoxide is required for the good yield of γ-butyrolactones.

KW - Blaise reaction intermediate

KW - Butyrolactone

KW - Epoxide opening

KW - Regioselectivity

KW - Tandem reaction

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DO - 10.1016/j.tetlet.2010.10.108

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SN - 0040-4039

VL - 51

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EP - 6896

JO - Tetrahedron Letters

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IS - 52

ER -

Tandem one-pot synthesis of α-(aminomethylene)-γ-butyrolactones via regioselective epoxide ring-opening with the Blaise reaction intermediate

Abstract

Bibliographical note

Keywords

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