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Enantioselective Synthesis of cis-1,2-Disubstituted Cyclopentanes and Cyclohexanes by Suzuki–Miyaura Cross-Coupling and Iridium-Catalyzed Asymmetric Hydrogenation

Schumacher, Andreas and Schrems, Markus and Pfaltz, ANdreas. (2011) Enantioselective Synthesis of cis-1,2-Disubstituted Cyclopentanes and Cyclohexanes by Suzuki–Miyaura Cross-Coupling and Iridium-Catalyzed Asymmetric Hydrogenation. Chemistry - A European Journal, 17 (48). pp. 13502-13509.

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Official URL: http://edoc.unibas.ch/dok/A5849085

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Abstract

A series of 1,2-disubstituted cyclohexene derivatives was prepared through Suzuki–Miyaura cross-coupling of 2-bromo-1-cyclohexenecarbaldehyde or 2-carbomethoxy-1-cyclohexen-1-yl triflate with arylboronates. These tetra-substituted cyclic alkenes were subjected to Ir-catalyzed asymmetric hydrogenation. In this way cis-1-methoxymethyl-2-arylcyclohexanes were obtained in high yield with excellent enantio- and diastereoselectivities (up to >99 % ee, >99 % cis) by using phosphinomethyloxazolines as ligands. Asymmetric hydrogenation of analogous cyclopentene derivatives, prepared by Suzuki–Miyaura cross-coupling, proved to be more difficult and proceeded with lower enantioselectivities of up to 88 % ee. The synthetic potential of this cross-coupling/asymmetric-hydrogenation strategy was demonstrated by an enantioselective route to chiral hexahydrofluorenones.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Synthetische organische Chemie (Pfaltz)
UniBasel Contributors:Pfaltz, Andreas
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Wiley
ISSN:0947-6539
e-ISSN:1521-3765
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:10 Apr 2017 10:05
Deposited On:14 Sep 2012 07:02

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