Acyclic stereocontrol in the catalytic C-H amination of benzylic methylene groups

Anike Nörder; Pavel Herrmann; Eberhard Herdtweck; Thorsten Bach

doi:10.1021/ol101517v

Acyclic stereocontrol in the catalytic C-H amination of benzylic methylene groups

Anike Nörder
, Pavel Herrmann
, Eberhard Herdtweck
, Thorsten Bach

Chair of Organic Chemistry 1

Technical University of Munich

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

35 Scopus citations

Abstract

Diastereotopos-differentiation is the key feature of the catalytic C-H amination at the benzylic position of substrate 1. Essentially independent of the functional group X (X = COOMe, PO(OEt)₂, SO₂Ph, NO₂, CN, OAc), the depicted products 2 are formed with good (dr = 80/20) to excellent (dr > 95/5) diastereoselectivity. The reaction proceeds without racemization and possesses potential for the C-H amination of open-chain substrates.

Original language	English
Pages (from-to)	3690-3692
Number of pages	3
Journal	Organic Letters
Volume	12
Issue number	16
DOIs	https://doi.org/10.1021/ol101517v
State	Published - 20 Aug 2010

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title = "Acyclic stereocontrol in the catalytic C-H amination of benzylic methylene groups",

abstract = "Diastereotopos-differentiation is the key feature of the catalytic C-H amination at the benzylic position of substrate 1. Essentially independent of the functional group X (X = COOMe, PO(OEt)2, SO2Ph, NO2, CN, OAc), the depicted products 2 are formed with good (dr = 80/20) to excellent (dr > 95/5) diastereoselectivity. The reaction proceeds without racemization and possesses potential for the C-H amination of open-chain substrates.",

author = "Anike N{\"o}rder and Pavel Herrmann and Eberhard Herdtweck and Thorsten Bach",

year = "2010",

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doi = "10.1021/ol101517v",

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T1 - Acyclic stereocontrol in the catalytic C-H amination of benzylic methylene groups

AU - Nörder, Anike

AU - Herrmann, Pavel

AU - Herdtweck, Eberhard

AU - Bach, Thorsten

PY - 2010/8/20

Y1 - 2010/8/20

N2 - Diastereotopos-differentiation is the key feature of the catalytic C-H amination at the benzylic position of substrate 1. Essentially independent of the functional group X (X = COOMe, PO(OEt)2, SO2Ph, NO2, CN, OAc), the depicted products 2 are formed with good (dr = 80/20) to excellent (dr > 95/5) diastereoselectivity. The reaction proceeds without racemization and possesses potential for the C-H amination of open-chain substrates.

AB - Diastereotopos-differentiation is the key feature of the catalytic C-H amination at the benzylic position of substrate 1. Essentially independent of the functional group X (X = COOMe, PO(OEt)2, SO2Ph, NO2, CN, OAc), the depicted products 2 are formed with good (dr = 80/20) to excellent (dr > 95/5) diastereoselectivity. The reaction proceeds without racemization and possesses potential for the C-H amination of open-chain substrates.

UR - https://www.scopus.com/pages/publications/77955687100

U2 - 10.1021/ol101517v

DO - 10.1021/ol101517v

M3 - Article

AN - SCOPUS:77955687100

SN - 1523-7060

VL - 12

SP - 3690

EP - 3692

JO - Organic Letters

JF - Organic Letters

IS - 16

ER -

Acyclic stereocontrol in the catalytic C-H amination of benzylic methylene groups

Abstract

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