Reaction of magnesium cyclopropylidene with N-lithio arylamines: a method for generation of α-amino-substituted cyclopropylmagnesiums and a study for their reactivity with electrophiles

Tsuyoshi Satoh; Mariko Miura; Ken Sakai; Yoshimi Yokoyama

doi:10.1016/j.tet.2006.01.080

Reaction of magnesium cyclopropylidene with N-lithio arylamines: a method for generation of α-amino-substituted cyclopropylmagnesiums and a study for their reactivity with electrophiles

Tsuyoshi Satoh, Mariko Miura, Ken Sakai, Yoshimi Yokoyama

Inorganic and Analytical Chemistry

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

40 Citations (Scopus)

Abstract

Magnesium cyclopropylidene was generated from 1-chlorocyclopropyl phenyl sulfoxide with i-PrMgCl in THF at -78 °C in high yield by a sulfoxide-magnesium exchange reaction. The generated magnesium cyclopropylidene was found to be reactive with N-lithio arylamines to give α-amino-substituted cyclopropylmagnesiums. The reaction of the α-amino-substituted cyclopropylmagnesiums with several electrophiles was examined and a new method for a synthesis of cyclopropane amino acid derivatives was realized.

Original language	English
Pages (from-to)	4253-4261
Number of pages	9
Journal	Tetrahedron
Volume	62
Issue number	17
DOIs	https://doi.org/10.1016/j.tet.2006.01.080
Publication status	Published - Apr 24 2006

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2006.01.080

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Reaction of magnesium cyclopropylidene with N-lithio arylamines : a method for generation of α-amino-substituted cyclopropylmagnesiums and a study for their reactivity with electrophiles. / Satoh, Tsuyoshi; Miura, Mariko; Sakai, Ken; Yokoyama, Yoshimi.

In: Tetrahedron, Vol. 62, No. 17, 24.04.2006, p. 4253-4261.

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

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AU - Sakai, Ken

AU - Yokoyama, Yoshimi

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AB - Magnesium cyclopropylidene was generated from 1-chlorocyclopropyl phenyl sulfoxide with i-PrMgCl in THF at -78 °C in high yield by a sulfoxide-magnesium exchange reaction. The generated magnesium cyclopropylidene was found to be reactive with N-lithio arylamines to give α-amino-substituted cyclopropylmagnesiums. The reaction of the α-amino-substituted cyclopropylmagnesiums with several electrophiles was examined and a new method for a synthesis of cyclopropane amino acid derivatives was realized.

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Reaction of magnesium cyclopropylidene with N-lithio arylamines: a method for generation of α-amino-substituted cyclopropylmagnesiums and a study for their reactivity with electrophiles

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