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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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.",

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T1 - Reaction of magnesium cyclopropylidene with N-lithio arylamines

T2 - a method for generation of α-amino-substituted cyclopropylmagnesiums and a study for their reactivity with electrophiles

AU - Satoh, Tsuyoshi

AU - Miura, Mariko

AU - Sakai, Ken

AU - Yokoyama, Yoshimi

PY - 2006/4/24

Y1 - 2006/4/24

N2 - 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.

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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JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

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ER -

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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