Download PDF
Synfacts 2014; 10(1): 0097
DOI: 10.1055/s-0033-1340380
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Regio- and Enantioselective Hydrogenation Using a Peptide Catalyst

Contributor(s):
Yasuhiro Uozumi
,
Go Hamasaka
Akagawa K, Sen J, Kudo K * The University of Tokyo, Japan
Peptide-Catalyzed Regio- and Enantioselective Reduction of α,β,γ,δ-Unsaturated Aldehydes.

Angew. Chem. Int. Ed. 2013;
52: 11585-11588
CrossrefSearch in Google Scholar
Further Information

Publication History

Publication Date:
13 December 2013 (online)

 PDF Download Permissions and Reprints

Key words

α,β,γ,δ-unsaturated aldehydes - Hantzsch esters - asymmetric transfer hydrogenation - peptide catalysis

Significance

The amphiphilic resin-supported peptide 1 catalyzed the regio- and enantioselective transfer hydrogenation of (2E,4E)-α,β,γ,δ-­unsaturated aldehydes 2 with a Hantzsch ester to give the corresponding aldehydes 3 in 47–87% yield with 87–99% ee (14 examples, eq. 1).


#

Comment

In the hydrogenation of the mixture of (2E,4E)-2b and (2Z,4E)-2b, aldehyde 3b was obtained in 71% yield with 97% ee (eq. 2). The authors have previously reported the asymmetric transfer hydrogenation of α,β-unsaturated aldehydes with a Hantzsch ester in the presence of resin-supported peptides (Org. Lett. 2008, 10, 2035; Tetrahedron: Asymmetry 2009, 20, 461).


#
#