Visible-light-mediated decarboxylative benzoyloxylation of β-hydroxy amino acids and its application to synthesis of functional 1,2-amino alcohol derivatives

Shinsuke Inuki; Keisuke Sato; Yukari Fujimoto

doi:10.1016/j.tetlet.2015.09.012

Visible-light-mediated decarboxylative benzoyloxylation of β-hydroxy amino acids and its application to synthesis of functional 1,2-amino alcohol derivatives

Shinsuke Inuki, Keisuke Sato, Yukari Fujimoto

Department of Chemistry

Research output: Contribution to journal › Article

4 Citations (Scopus)

Abstract

We have developed a novel method for decarboxylative benzoyloxylation of β-hydroxy amino acids using photoredox catalyst Ru(bpy)<inf>3</inf>Cl<inf>2</inf>·6H<inf>2</inf>O and benzoylperoxide (BzO)<inf>2</inf>. This strategy was expanded to the synthesis of structurally diverse chiral 1,2-amino alcohols with different aryl or alkyl groups, starting from serine or threonine derivatives.

Original language	English
Pages (from-to)	5787-5790
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	42
DOIs	https://doi.org/10.1016/j.tetlet.2015.09.012
Publication status	Published - 2015 Oct 14

Fingerprint

Keywords

Amino alcohols
N-Acyliminium
Photocatalysis
Ruthenium
Visible light

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

Cite this

Inuki, S., Sato, K., & Fujimoto, Y. (2015). Visible-light-mediated decarboxylative benzoyloxylation of β-hydroxy amino acids and its application to synthesis of functional 1,2-amino alcohol derivatives. Tetrahedron Letters, 56(42), 5787-5790. https://doi.org/10.1016/j.tetlet.2015.09.012

@article{ff2dd61bdd0d47a2968c978d944b69ee,

title = "Visible-light-mediated decarboxylative benzoyloxylation of β-hydroxy amino acids and its application to synthesis of functional 1,2-amino alcohol derivatives",

abstract = "We have developed a novel method for decarboxylative benzoyloxylation of β-hydroxy amino acids using photoredox catalyst Ru(bpy)3Cl2·6H2O and benzoylperoxide (BzO)2. This strategy was expanded to the synthesis of structurally diverse chiral 1,2-amino alcohols with different aryl or alkyl groups, starting from serine or threonine derivatives.",

keywords = "Amino alcohols, N-Acyliminium, Photocatalysis, Ruthenium, Visible light",

author = "Shinsuke Inuki and Keisuke Sato and Yukari Fujimoto",

year = "2015",

month = oct,

day = "14",

doi = "10.1016/j.tetlet.2015.09.012",

language = "English",

volume = "56",

pages = "5787--5790",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "42",

}

TY - JOUR

T1 - Visible-light-mediated decarboxylative benzoyloxylation of β-hydroxy amino acids and its application to synthesis of functional 1,2-amino alcohol derivatives

AU - Inuki, Shinsuke

AU - Sato, Keisuke

AU - Fujimoto, Yukari

PY - 2015/10/14

Y1 - 2015/10/14

N2 - We have developed a novel method for decarboxylative benzoyloxylation of β-hydroxy amino acids using photoredox catalyst Ru(bpy)3Cl2·6H2O and benzoylperoxide (BzO)2. This strategy was expanded to the synthesis of structurally diverse chiral 1,2-amino alcohols with different aryl or alkyl groups, starting from serine or threonine derivatives.

AB - We have developed a novel method for decarboxylative benzoyloxylation of β-hydroxy amino acids using photoredox catalyst Ru(bpy)3Cl2·6H2O and benzoylperoxide (BzO)2. This strategy was expanded to the synthesis of structurally diverse chiral 1,2-amino alcohols with different aryl or alkyl groups, starting from serine or threonine derivatives.

KW - Amino alcohols

KW - N-Acyliminium

KW - Photocatalysis

KW - Ruthenium

KW - Visible light

UR - http://www.scopus.com/inward/record.url?scp=84941995425&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84941995425&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2015.09.012

DO - 10.1016/j.tetlet.2015.09.012

M3 - Article

AN - SCOPUS:84941995425

VL - 56

SP - 5787

EP - 5790

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 42

ER -

Access to Document

10.1016/j.tetlet.2015.09.012