Stereoselective synthesis of chiral thiol-containing 1,2-aminoalcohols via SmI2-mediated coupling

Carina Doler; Michael Friess; Florian Lackner; Hansjörg Weber; Roland C. Fischer; Rolf Breinbauer

doi:10.1016/j.tet.2020.131249

Stereoselective synthesis of chiral thiol-containing 1,2-aminoalcohols via SmI₂-mediated coupling

Carina Doler, Michael Friess, Florian Lackner, Hansjörg Weber, Roland C. Fischer, Rolf Breinbauer^*

^*Corresponding author for this work

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

Abstract

The stereoselective synthesis of highly functionalized aminohydroxythiols represents a synthetic challenge as the oxidation sensitivity and coordinating property of the thiol group interferes with many established synthetic methods. The SmI₂/LiBr-mediated reductive coupling between Ellman N-sulfinylimines, containing thiol groups protected either as trityl thioether or dihydrothiazolidine, and aldehydes enables the synthesis of chiral aminohydroxythiols in high enantio- and diastereoselectivity. The scope of this reaction has been established for 18 examples and applied for the synthesis of a complex intermediate needed for a biosynthesis study.

Original language	English
Article number	131249
Journal	Tetrahedron
Volume	76
Issue number	51
DOIs	https://doi.org/10.1016/j.tet.2020.131249
Publication status	Published - 18 Dec 2020

Keywords

Asymmetric synthesis
Chiral auxiliary
Ellman reagent
Reductive coupling
Samarium diiodide
Sharpless aminohydroxylation
Single electron transfer

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Fields of Expertise

Human- & Biotechnology

Access to Document

10.1016/j.tet.2020.131249Licence: CC BY 4.0

Cite this

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title = "Stereoselective synthesis of chiral thiol-containing 1,2-aminoalcohols via SmI2-mediated coupling",

abstract = "The stereoselective synthesis of highly functionalized aminohydroxythiols represents a synthetic challenge as the oxidation sensitivity and coordinating property of the thiol group interferes with many established synthetic methods. The SmI2/LiBr-mediated reductive coupling between Ellman N-sulfinylimines, containing thiol groups protected either as trityl thioether or dihydrothiazolidine, and aldehydes enables the synthesis of chiral aminohydroxythiols in high enantio- and diastereoselectivity. The scope of this reaction has been established for 18 examples and applied for the synthesis of a complex intermediate needed for a biosynthesis study.",

keywords = "Asymmetric synthesis, Chiral auxiliary, Ellman reagent, Reductive coupling, Samarium diiodide, Sharpless aminohydroxylation, Single electron transfer",

author = "Carina Doler and Michael Friess and Florian Lackner and Hansj{\"o}rg Weber and Fischer, {Roland C.} and Rolf Breinbauer",

year = "2020",

month = dec,

day = "18",

doi = "10.1016/j.tet.2020.131249",

language = "English",

volume = "76",

journal = "Tetrahedron",

issn = "0040-4020",

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number = "51",

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TY - JOUR

T1 - Stereoselective synthesis of chiral thiol-containing 1,2-aminoalcohols via SmI2-mediated coupling

AU - Doler, Carina

AU - Friess, Michael

AU - Lackner, Florian

AU - Weber, Hansjörg

AU - Fischer, Roland C.

AU - Breinbauer, Rolf

PY - 2020/12/18

Y1 - 2020/12/18

N2 - The stereoselective synthesis of highly functionalized aminohydroxythiols represents a synthetic challenge as the oxidation sensitivity and coordinating property of the thiol group interferes with many established synthetic methods. The SmI2/LiBr-mediated reductive coupling between Ellman N-sulfinylimines, containing thiol groups protected either as trityl thioether or dihydrothiazolidine, and aldehydes enables the synthesis of chiral aminohydroxythiols in high enantio- and diastereoselectivity. The scope of this reaction has been established for 18 examples and applied for the synthesis of a complex intermediate needed for a biosynthesis study.

AB - The stereoselective synthesis of highly functionalized aminohydroxythiols represents a synthetic challenge as the oxidation sensitivity and coordinating property of the thiol group interferes with many established synthetic methods. The SmI2/LiBr-mediated reductive coupling between Ellman N-sulfinylimines, containing thiol groups protected either as trityl thioether or dihydrothiazolidine, and aldehydes enables the synthesis of chiral aminohydroxythiols in high enantio- and diastereoselectivity. The scope of this reaction has been established for 18 examples and applied for the synthesis of a complex intermediate needed for a biosynthesis study.

KW - Asymmetric synthesis

KW - Chiral auxiliary

KW - Ellman reagent

KW - Reductive coupling

KW - Samarium diiodide

KW - Sharpless aminohydroxylation

KW - Single electron transfer

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U2 - 10.1016/j.tet.2020.131249

DO - 10.1016/j.tet.2020.131249

M3 - Article

AN - SCOPUS:85084410754

SN - 0040-4020

VL - 76

JO - Tetrahedron

JF - Tetrahedron

IS - 51

M1 - 131249

ER -

Stereoselective synthesis of chiral thiol-containing 1,2-aminoalcohols via SmI₂-mediated coupling

Abstract

Keywords

ASJC Scopus subject areas

Fields of Expertise

Access to Document

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FWF - RETROBIO - A twofold retrosynthetic implementation of a novel biochemical pathway (RETROBIO)

Cite this

Stereoselective synthesis of chiral thiol-containing 1,2-aminoalcohols via SmI2-mediated coupling

Abstract

Keywords

ASJC Scopus subject areas

Fields of Expertise

Access to Document

Other files and links

Fingerprint

Projects

FWF - RETROBIO - A twofold retrosynthetic implementation of a novel biochemical pathway (RETROBIO)

Cite this

Stereoselective synthesis of chiral thiol-containing 1,2-aminoalcohols via SmI₂-mediated coupling