Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2009 May;8(2009):1189-1207.
doi: 10.1055/s-0029-1216654.

The Catalytic Asymmetric Intramolecular Stetter Reaction

Javier Read de Alaniz  1 , Tomislav Rovis
Affiliations

The Catalytic Asymmetric Intramolecular Stetter Reaction

Javier Read de Alaniz et al. Synlett. 2009 May.

Abstract

This account chronicles our efforts at the development of a catalytic asymmetric Stetter reaction using chiral triazolium salts as small molecule organic catalysts. Advances in the mechanistically related azolium-catalyzed asymmetric benzoin reaction are discussed, particularly as they apply to catalyst design. A chronological treatise of reaction discovery, catalyst optimization and reactivity extension follows.

PubMed Disclaimer

Figures

Figure 1
Figure 1
The benzoin and Stetter reaction
Scheme 1
Scheme 1
Proposed mechanism of the benzoin and Stetter reactions.
Scheme 2
Scheme 2
Catalysts for the asymmetric benzoin reaction
Scheme 3
Scheme 3
The enantioselective cross silyl benzoin reaction
Scheme 4
Scheme 4
Designing new chiral bicyclic triazolium scaffolds
Scheme 5
Scheme 5
Synthesis of aminoindanol-derived triazolium salts.
Scheme 6
Scheme 6
The synthesis of phenylalanine-derived triazolium salts.
Scheme 7
Scheme 7
The first asymmetric intermolecular Stetter seaction.
Scheme 8
Scheme 8
Asymmetric intermolecular Stetter reaction of acyl silanes.
Scheme 9
Scheme 9
The first detailed study of the intramolecular Stetter reaction.
Scheme 10
Scheme 10
The first asymmetric intramolecular Stetter reaction
Scheme 11
Scheme 11
Bach's asymmetric intramolecular Stetter reaction.
Scheme 12
Scheme 12
Chiral peptide derived thiazolium salts
Scheme 13
Scheme 13
The optimal peptide derived catalyst for the asymmetric Stetter reaction
Scheme 14
Scheme 14
The asymmetric intramolucular Stetter reaction utilizing C2-symmetric imidazolidene carbene.
Scheme 15
Scheme 15
Initial results in the asymmetric intramolecular Stetter reaction.
Scheme 16
Scheme 16
Initial discovery of the enantio- and diastereoselective intramolecular Stetter reaction.
Scheme 17
Scheme 17
Optimization of the enantio- and diastereoselective intramolecular Stetter reaction.
Scheme 18
Scheme 18
Control of the relative diastereoselectivity depending on the alkene geometry.
Scheme 19
Scheme 19
Possible intermediates for the enantio- and diastereoselective intramolecular Stetter reaction
Scheme 20
Scheme 20
Model study approach to FD-838.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. For reviews, see: Regitz M. Angew. Chem., Int. Ed. Engl. 1996;35:725.. Bourissou D, Guerret O, Gabbai FP, Bertrand G. Chem. Rev. 2000;100:39.. Herrmann WA. Angew. Chem. Int. Ed. 2002;41:1291..

    1. For reviews, see: Enders D, Balensiefer T. Acc. Chem. Res. 2004;37:534.. Johnson JS. Angew. Chem. Int. Ed. 2004;43:1326.. Pohl M, Lingen B, Müller M. Chem. Eur. J. 2002;8:5288.. Nair V, Bindu S, Sreekumar V. Angew. Chem. Int. Ed. 2004;43:5130.. Zeitler K. Angew. Chem. Int. Ed. 2004;43:7506.. Christmann M. Angew. Chem. Int. Ed. 2005;44:2632.. Webber P, Krische MJ. Chemtracts: Org. Chem. 2007;19:262..

    1. Seebach D. Angew. Chem., Int. Ed. Engl. 1979;18:239.

    1. For reviews, see: Albright JD. Tetrahedron. 1983;39:3207.. Aitken RA, Thomas AW. Adv. Heterocyclic Chem. 2001;79:89..

    1. For examples of the benzoin reaction that are not referenced later in the text, see; Hachisu Y, Bode JW, Suzuki K. J. Am. Chem. Soc. 2003;125:8432.. Enders D, Niemeier O, Balensiefer T. Angew. Chem. Int. Ed. 2006;45:1463.. For examples of the benzoin reaction with acyl silanes see; Linghu X, Johnson JS. Angew. Chem. Int Ed. 2003;42:2534.. Linghu X, Potnick JR, Johnson JS. J. Am. Chem. Soc. 2004;126:3070.

LinkOut - more resources