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. 2008 Oct 2;10(19):4231-4.
doi: 10.1021/ol801605w. Epub 2008 Sep 3.

Cu(I)-catalyzed asymmetric diamination of conjugated dienes

Haifeng Du  1 , Baoguo Zhao, Weicheng Yuan, Yian Shi
Affiliations

Cu(I)-catalyzed asymmetric diamination of conjugated dienes

Haifeng Du et al. Org Lett. .

Abstract

A Cu(I)-catalyzed asymmetric diamination for a variety of conjugated dienes and a triene with encouraging ee's has been effectively achieved using (R)-DTBM-SEGPHOS as a chiral ligand and di- tert-butyldiaziridinone as the nitrogen source.

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Figures

Figure 1
Figure 1
A Proposed Catalytic Cycle for Cu(I)-catalyzed Diamination
Figure 2
Figure 2
Asymmetric Diamination of Diene 7a with Selected Monophosphorus and Nitrogen-containing Ligands
Figure 3
Figure 3
Asymmetric Diamination of Diene 7a with Selected Bisphosphine Ligands
Scheme 1
Scheme 1
Scheme 2
Scheme 2
See this image and copyright information in PMC

References

    1. For leading reviews, see: Lucet D, Gall TL, Mioskowski C. Angew. Chem., Int. Ed. 1998;37:2580. Mortensen MS, O’Doherty GA. Chemtracts: Organic Chemistry. 2005;18:555. Kotti SRSS, Timmons C, Li G. Chem. Biol. Drug. Des. 2006;67:101.

    1. For examples of metal-mediated diaminations, see: Co: Becker PN, White MA, Bergman RG. J. Am. Chem. Soc. 1980;102:5676. Hg: Barluenga J, Alonso-Cires L, Asensio G. Synthesis. 1979;962:962. Mn: Fristad WE, Brandvold TA, Peterson JR, Thompson SR. J. Org. Chem. 1985;50:3647. Os: Chong AO, Oshima K, Sharpless KB. J. Am. Chem. Soc. 1977;99:3420. Muñiz K. Eur. J. Org. Chem. 2004:2243. Pd: Bäckvall J-E. Tetrahedron Lett. 1978:163. Tl: Aranda VG, Barluenga J, Aznar F. Synthesis. 1974:504.

    1. For recent Cu(II)-mediated intramolecular diamination, see: Zabawa TP, Kasi D, Chemler SR. J. Am. Chem. Soc. 2005;127:11250. Zabawa TP, Chemler SR. Org. Lett. 2007;9:2035.

    1. For Rh(II)-, Fe(III)-catalyzed diamination with TsNCl2, see: Li G, Wei H-X, Kim SH, Carducci MD. Angew. Chem., Int. Ed. 2001;40:4277. Wei H-X, Kim SH, Li G. J. Org. Chem. 2002;67:4777.

    1. For a recent Pd(II)-catalyzed intermolecular diamination of conjugated dienes, see: Bar GLJ, Lloyd-Jones GC, Booker-Milburn KI. J. Am. Chem. Soc. 2005;127:7308.

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