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

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

Fingerprint

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Satoh, T., Miura, M., Sakai, K., & Yokoyama, Y. (2006). 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. Tetrahedron, 62(17), 4253-4261. https://doi.org/10.1016/j.tet.2006.01.080

@article{3ff8e0285d744fb5aaba4d8731c2e49a,

title = "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",

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.",

author = "Tsuyoshi Satoh and Mariko Miura and Ken Sakai and Yoshimi Yokoyama",

year = "2006",

month = "4",

day = "24",

doi = "10.1016/j.tet.2006.01.080",

language = "English",

volume = "62",

pages = "4253--4261",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "17",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=33645965855&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33645965855&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2006.01.080

DO - 10.1016/j.tet.2006.01.080

M3 - Article

AN - SCOPUS:33645965855

VL - 62

SP - 4253

EP - 4261

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 17

ER -

Access to Document

10.1016/j.tet.2006.01.080