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En route to new chiral ferrocene derivatives: dead ends, detours, and avenues

En route to new chiral ferrocene derivatives: dead ends, detours, and avenues
En route to new chiral ferrocene derivatives: dead ends, detours, and avenues
The enantioselective synthesis of ?-amino-?-ferrocenyl alcohols, a new class of chiral ferrocene derivatives suitable for the elaboration of auxiliaries and ligands for asymmetric synthesis, can be efficiently achieved by the catalytic asymmetric dihydroxylation of 1-ferrocenylalkenes, followed by the regio- and stereoselective substitution of the hydroxy group adjacent to the ferrocene moiety by nitrogen nucleophiles. En route to these compounds, several previously unknown metallocene derivatives such as ?-ferrocenyl epoxides, interannularly cyclopalladated ferrocenyloxazolines, and ?-amino-?-ferrocenyl acids have been obtained. The first examples of an organocatalytic approach to the enantioselective synthesis of chiral ferrocenes are also presented.
amino alcohols, asymmetric catalysis, epoxides, ferrocenes, palladacycles
0936-5214
1863-1886
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441

Moyano, Albert and Rios, Ramon (2009) En route to new chiral ferrocene derivatives: dead ends, detours, and avenues. Synlett, 2009 (12), 1863-1886. (doi:10.1055/s-0029-1217514).

Record type: Article

Abstract

The enantioselective synthesis of ?-amino-?-ferrocenyl alcohols, a new class of chiral ferrocene derivatives suitable for the elaboration of auxiliaries and ligands for asymmetric synthesis, can be efficiently achieved by the catalytic asymmetric dihydroxylation of 1-ferrocenylalkenes, followed by the regio- and stereoselective substitution of the hydroxy group adjacent to the ferrocene moiety by nitrogen nucleophiles. En route to these compounds, several previously unknown metallocene derivatives such as ?-ferrocenyl epoxides, interannularly cyclopalladated ferrocenyloxazolines, and ?-amino-?-ferrocenyl acids have been obtained. The first examples of an organocatalytic approach to the enantioselective synthesis of chiral ferrocenes are also presented.

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More information

Published date: 2009
Keywords: amino alcohols, asymmetric catalysis, epoxides, ferrocenes, palladacycles
Organisations: Chemistry

Identifiers

Local EPrints ID: 347742
URI: http://eprints.soton.ac.uk/id/eprint/347742
ISSN: 0936-5214
PURE UUID: 5f94928a-5da6-415f-95f8-1ff60589db85
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 29 Jan 2013 14:15
Last modified: 20 Jul 2019 00:42

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