Generation of boron Aza-enolates by a nickel-catalyzed reaction of triazoles with pinacolborane and their addition to aldehydes

Tomoya Miura; Sho Miyakawa; Takayuki Nakamuro; Masahiro Murakami

doi:10.1246/cl.190290

Generation of boron Aza-enolates by a nickel-catalyzed reaction of triazoles with pinacolborane and their addition to aldehydes

Tomoya Miura, Sho Miyakawa, Takayuki Nakamuro, Masahiro Murakami

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

Abstract

An aldol-type reaction of boron aza-enolates with aldehydes is reported. N-Sulfonyl-1,2,3-triazoles react with pinacolborane in the presence of a nickel(0) catalyst to generate boron azaenolates with E geometry. The boron aza-enolates undergo an aldol-type reaction with aldehydes to give β-boroxy imines with syn configuration. The subsequent one-pot reduction with DIBALH gives 1,3-amino alcohols.

Original language	English
Pages (from-to)	965-967
Number of pages	3
Journal	Chemistry Letters
Volume	48
Issue number	8
DOIs	https://doi.org/10.1246/cl.190290
Publication status	Published - 2019
Externally published	Yes

Keywords

Boron aza-enolates
Nickel
Triazoles

ASJC Scopus subject areas

Chemistry(all)

Access to Document

10.1246/cl.190290

Cite this

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title = "Generation of boron Aza-enolates by a nickel-catalyzed reaction of triazoles with pinacolborane and their addition to aldehydes",

abstract = "An aldol-type reaction of boron aza-enolates with aldehydes is reported. N-Sulfonyl-1,2,3-triazoles react with pinacolborane in the presence of a nickel(0) catalyst to generate boron azaenolates with E geometry. The boron aza-enolates undergo an aldol-type reaction with aldehydes to give β-boroxy imines with syn configuration. The subsequent one-pot reduction with DIBALH gives 1,3-amino alcohols.",

keywords = "Boron aza-enolates, Nickel, Triazoles",

author = "Tomoya Miura and Sho Miyakawa and Takayuki Nakamuro and Masahiro Murakami",

note = "Funding Information: We thank Dr. Y. Nagata (Kyoto University) for his kind help in an X-ray crystallographic analysis. This work was supported by MEXT [Grants-in-Aids for Scientific Research (S) (15H05756, MM) and (C) (16K05694, TM)]. Publisher Copyright: {\textcopyright} 2019 The Chemical Society of Japan.",

year = "2019",

doi = "10.1246/cl.190290",

language = "English",

volume = "48",

pages = "965--967",

journal = "Chemistry Letters",

issn = "0366-7022",

publisher = "Chemical Society of Japan",

number = "8",

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TY - JOUR

T1 - Generation of boron Aza-enolates by a nickel-catalyzed reaction of triazoles with pinacolborane and their addition to aldehydes

AU - Miura, Tomoya

AU - Miyakawa, Sho

AU - Nakamuro, Takayuki

AU - Murakami, Masahiro

N1 - Funding Information: We thank Dr. Y. Nagata (Kyoto University) for his kind help in an X-ray crystallographic analysis. This work was supported by MEXT [Grants-in-Aids for Scientific Research (S) (15H05756, MM) and (C) (16K05694, TM)]. Publisher Copyright: © 2019 The Chemical Society of Japan.

PY - 2019

Y1 - 2019

N2 - An aldol-type reaction of boron aza-enolates with aldehydes is reported. N-Sulfonyl-1,2,3-triazoles react with pinacolborane in the presence of a nickel(0) catalyst to generate boron azaenolates with E geometry. The boron aza-enolates undergo an aldol-type reaction with aldehydes to give β-boroxy imines with syn configuration. The subsequent one-pot reduction with DIBALH gives 1,3-amino alcohols.

AB - An aldol-type reaction of boron aza-enolates with aldehydes is reported. N-Sulfonyl-1,2,3-triazoles react with pinacolborane in the presence of a nickel(0) catalyst to generate boron azaenolates with E geometry. The boron aza-enolates undergo an aldol-type reaction with aldehydes to give β-boroxy imines with syn configuration. The subsequent one-pot reduction with DIBALH gives 1,3-amino alcohols.

KW - Boron aza-enolates

KW - Nickel

KW - Triazoles

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U2 - 10.1246/cl.190290

DO - 10.1246/cl.190290

M3 - Article

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SN - 0366-7022

VL - 48

SP - 965

EP - 967

JO - Chemistry Letters

JF - Chemistry Letters

IS - 8

ER -

Generation of boron Aza-enolates by a nickel-catalyzed reaction of triazoles with pinacolborane and their addition to aldehydes

Abstract

Keywords

ASJC Scopus subject areas

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