Synthesis of 1,2-amino alcohols via catalytic C–H amidation of sp3 methyl C

Synthesis of 1,2-amino alcohols via catalytic C–H amidation of sp3 methyl C–H bonds

Published:2014 Issue:81 Volume:50 Page:12073-12075
ISSN:1359-7345
Container-title:Chem. Commun.
language:en
Short-container-title:Chem. Commun.

Author:

Kang Taek¹²³⁴⁵,Kim Heejeong⁴⁵³¹²,Kim Jeung Gon¹²³⁴⁵,Chang Sukbok¹²³⁴⁵

Affiliation:

1. Center for Catalytic Hydrocarbon Functionalizations

2. Institute for Basic Science

3. Daejeon 305-701, Korea

4. Department of Chemistry

5. Korea Advanced Institute of Science and Technology

Abstract

A new route to 1,2-amino alcohols is presented by C–H amidation of sp³ methyl C–H bonds as a key step. Various alcohols were employed after converting them to removable ketoxime chelating groups. Iridium-catalyzed C–H amidation and following LAH reduction furnished β-amino alcohol products.

Publisher

Royal Society of Chemistry (RSC)

Subject

Materials Chemistry,Metals and Alloys,Surfaces, Coatings and Films,General Chemistry,Ceramics and Composites,Electronic, Optical and Magnetic Materials,Catalysis

Link

http://pubs.rsc.org/en/content/articlepdf/2014/CC/C4CC05655H

Reference55 articles.

1. The Synthesis of Vicinal Amino Alcohols

2. 1,2-Amino Alcohols and Their Heterocyclic Derivatives as Chiral Auxiliaries in Asymmetric Synthesis

3. Diastereoselective synthesis of vicinal amino alcohols

4. The Henry reaction: recent examples

5. New Approaches to the Use of Amino Acids as Chiral Building Blocks in Organic Synthesis[New Synthetic Methods(85)]

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