Tetrahedron

, volume 64 , issue 27 , pages 6415-6419

First asymmetric Abramov-type phosphonylation of aldehydes with trialkyl phosphites catalyzed by chiral Lewis bases

Kyoko NAKANISHI ^{1, 2}

Shunsuke Kotani ^{1, 2}

Masaharu Sugiura ^{1, 2}

Makoto NAKAJIMA ^{1, 2}

Hide authors affiliations Show authors affiliations: 2 affiliations

Faculty of Medical and Pharmaceutical Sciences, Kumamoto University |

5-1 Oe-honmachi, Kumamoto 862-0973, Japan. |

Publication type: Journal Article

Publication date: 2008-06-01

Elsevier

Tetrahedron

scimago Q3

wos Q2

SJR: 0.426

CiteScore: 4.1

Impact factor: 2.2

ISSN: 00404020, 14645416

DOI: 10.1016/j.tet.2008.04.078

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Organic Chemistry

Drug Discovery

Biochemistry

Abstract

Abstract Chiral phosphine oxides (Lewis bases) catalyze silicon tetrachloride-mediated, enantioselective phosphonylation of aldehydes with trialkyl phosphites (Abramov-type reaction), which leads to optically active α-hydroxyphosphonates with moderate enantioselectivities. 31P NMR analysis of the phosphonylation of benzaldehyde with triethyl phosphite supports the assumed reaction mechanism.

Found

1 citation

Gavrilov Konstantin

DSc in Chemistry, professor

149 publications, 1 766 citations

h-index: 20

Ryazan State University named after S. A. Esenin

Research interests

Asymmetric metal complex catalysis

Asymmetric synthesis

Complex formation

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GOST |

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GOST Copy

NAKANISHI K. et al. First asymmetric Abramov-type phosphonylation of aldehydes with trialkyl phosphites catalyzed by chiral Lewis bases // Tetrahedron. 2008. Vol. 64. No. 27. pp. 6415-6419.

GOST all authors (up to 50) Copy

NAKANISHI K., Kotani S., Sugiura M., NAKAJIMA M. First asymmetric Abramov-type phosphonylation of aldehydes with trialkyl phosphites catalyzed by chiral Lewis bases // Tetrahedron. 2008. Vol. 64. No. 27. pp. 6415-6419.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1016/j.tet.2008.04.078

UR - https://doi.org/10.1016/j.tet.2008.04.078

TI - First asymmetric Abramov-type phosphonylation of aldehydes with trialkyl phosphites catalyzed by chiral Lewis bases

T2 - Tetrahedron

AU - NAKANISHI, Kyoko

AU - Kotani, Shunsuke

AU - Sugiura, Masaharu

AU - NAKAJIMA, Makoto

PY - 2008

DA - 2008/06/01

PB - Elsevier

SP - 6415-6419

IS - 27

VL - 64

SN - 0040-4020

SN - 1464-5416

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2008_NAKANISHI,

author = {Kyoko NAKANISHI and Shunsuke Kotani and Masaharu Sugiura and Makoto NAKAJIMA},

title = {First asymmetric Abramov-type phosphonylation of aldehydes with trialkyl phosphites catalyzed by chiral Lewis bases},

journal = {Tetrahedron},

year = {2008},

volume = {64},

publisher = {Elsevier},

month = {jun},

url = {https://doi.org/10.1016/j.tet.2008.04.078},

number = {27},

pages = {6415--6419},

doi = {10.1016/j.tet.2008.04.078}

}

MLA

Cite this

MLA Copy

NAKANISHI, Kyoko, et al. “First asymmetric Abramov-type phosphonylation of aldehydes with trialkyl phosphites catalyzed by chiral Lewis bases.” Tetrahedron, vol. 64, no. 27, Jun. 2008, pp. 6415-6419. https://doi.org/10.1016/j.tet.2008.04.078.

Publisher

Elsevier

Journal

Tetrahedron

scimago Q3

wos Q2

SJR

0.426

CiteScore

4.1

Impact factor

2.2

ISSN

00404020 (Print)

14645416 (Electronic)