Asymmetric synthesis of cyclopropylmethanamines by rhodium-catalyzed cyclopropanation of pinacol allylboronate with N-sulfonyl-1,2,3-triazoles

Tomoya Miura; Takayuki Nakamuro; Hiroki Nikishima; Masahiro Murakami

doi:10.1246/cl.160465

Asymmetric synthesis of cyclopropylmethanamines by rhodium-catalyzed cyclopropanation of pinacol allylboronate with N-sulfonyl-1,2,3-triazoles

Tomoya Miura, Takayuki Nakamuro, Hiroki Nikishima, Masahiro Murakami

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

9 Citations (Scopus)

Abstract

Herein, the rhodium(II)-catalyzed cyclopropanation reaction of pinacol allylboronate with N-sulfonyl-1,2,3-triazoles is reported. Boryl-substituted cyclopropylmethanamines are produced in a highly diastereo- and enantioselective manner. Various cyclopropylmethanamines containing a quaternary stereocenter are derived from them.

Original language	English
Pages (from-to)	1003-1005
Number of pages	3
Journal	Chemistry Letters
Volume	45
Issue number	8
DOIs	https://doi.org/10.1246/cl.160465
Publication status	Published - 2016
Externally published	Yes

Keywords

Cyclopropylmethanamine
Rhodium catalyst
Triazole

ASJC Scopus subject areas

Chemistry(all)

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10.1246/cl.160465

Cite this

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title = "Asymmetric synthesis of cyclopropylmethanamines by rhodium-catalyzed cyclopropanation of pinacol allylboronate with N-sulfonyl-1,2,3-triazoles",

abstract = "Herein, the rhodium(II)-catalyzed cyclopropanation reaction of pinacol allylboronate with N-sulfonyl-1,2,3-triazoles is reported. Boryl-substituted cyclopropylmethanamines are produced in a highly diastereo- and enantioselective manner. Various cyclopropylmethanamines containing a quaternary stereocenter are derived from them.",

keywords = "Cyclopropylmethanamine, Rhodium catalyst, Triazole",

author = "Tomoya Miura and Takayuki Nakamuro and Hiroki Nikishima and Masahiro Murakami",

note = "Funding Information: This work was supported in part by Grants-in-Aid for Scientific Research (S) (No. 15H05756) and (C) (No. 16K05694) from MEXT. T.N. acknowledged JSPS fellowship for young scientists. Publisher Copyright: {\textcopyright} 2016 The Chemical Society of Japan.",

year = "2016",

doi = "10.1246/cl.160465",

language = "English",

volume = "45",

pages = "1003--1005",

journal = "Chemistry Letters",

issn = "0366-7022",

publisher = "Chemical Society of Japan",

number = "8",

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TY - JOUR

T1 - Asymmetric synthesis of cyclopropylmethanamines by rhodium-catalyzed cyclopropanation of pinacol allylboronate with N-sulfonyl-1,2,3-triazoles

AU - Miura, Tomoya

AU - Nakamuro, Takayuki

AU - Nikishima, Hiroki

AU - Murakami, Masahiro

N1 - Funding Information: This work was supported in part by Grants-in-Aid for Scientific Research (S) (No. 15H05756) and (C) (No. 16K05694) from MEXT. T.N. acknowledged JSPS fellowship for young scientists. Publisher Copyright: © 2016 The Chemical Society of Japan.

PY - 2016

Y1 - 2016

N2 - Herein, the rhodium(II)-catalyzed cyclopropanation reaction of pinacol allylboronate with N-sulfonyl-1,2,3-triazoles is reported. Boryl-substituted cyclopropylmethanamines are produced in a highly diastereo- and enantioselective manner. Various cyclopropylmethanamines containing a quaternary stereocenter are derived from them.

AB - Herein, the rhodium(II)-catalyzed cyclopropanation reaction of pinacol allylboronate with N-sulfonyl-1,2,3-triazoles is reported. Boryl-substituted cyclopropylmethanamines are produced in a highly diastereo- and enantioselective manner. Various cyclopropylmethanamines containing a quaternary stereocenter are derived from them.

KW - Cyclopropylmethanamine

KW - Rhodium catalyst

KW - Triazole

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DO - 10.1246/cl.160465

M3 - Article

AN - SCOPUS:85011968943

SN - 0366-7022

VL - 45

SP - 1003

EP - 1005

JO - Chemistry Letters

JF - Chemistry Letters

IS - 8

ER -

Asymmetric synthesis of cyclopropylmethanamines by rhodium-catalyzed cyclopropanation of pinacol allylboronate with N-sulfonyl-1,2,3-triazoles

Abstract

Keywords

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