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;48(20):3648-52.
doi: 10.1002/anie.200900236.

Complex allylation by the direct cross-coupling of imines with unactivated allylic alcohols

Masayuki Takahashi  1 , Martin McLaughlin, Glenn C Micalizio
Affiliations

Complex allylation by the direct cross-coupling of imines with unactivated allylic alcohols

Masayuki Takahashi et al. Angew Chem Int Ed Engl. 2009.

Abstract

Regioselective, stereoselective: The convergent coupling of allylic alcohols with imines to deliver stereodefined homoallylic amines is described (see scheme). The process proceeds with net allylic transposition without the intermediacy of allylic organometallic reagents. Two stereodefined centers and a geometrically defined di- or trisubstituted alkene are forged with high selectivity.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Allylation for convergent C–C bond formation.
Figure 2
Figure 2
Reaction design.
Figure 3
Figure 3
Empirical model for regio- and stereoselection.
See this image and copyright information in PMC

References

    1. For a discussion of strategy in complex molecule synthesis, along with detailed case studies, see: Corey EJ, Cheng X-M. The Logic of Chemical Synthesis. John Wiley & Sons, Inc; New York: 1989. Nicolaou KC, Sorensen EJ. Classics in Total Synthesis. VCH; New York: 1996.

    1. For a recent review of advances in catalysis, see: Cornils B, Herrmann WA, Muhler M, Wong C-H. Catalysis from A to Z. Wiley-VCH; New York: 2007.

    1. For a current review of allylation chemistry, see: Denmark SE, Almstead NG. In: Modern Carbonyl Chemistry. Otera J, editor. Wiley-VCH; New York: 2000. p. 299.For a current review on the application of the allylation reaction to the synthesis of natural products, see: Chemler SR, Roush WR. In: Modern Carbonyl Chemistry. Otera J, editor. Wiley-VCH; New York: 2000. p. 403.

    1. Notable exceptions include bifunctionalized allylmetal reagents and complex crotylsilanes. For recent discussions, see: Flamme EM, Roush WR. J Am Chem Soc. 2002;124:13644.and references therein; and Masse CE, Panek JS. Chem Rev. 1995;95:1293.

    1. For a review of catalyt enantioselective addition of allylic organometallic reagents to aldehydes and ketones, see: Denmark SE, Fu J. Chem Rev. 2003;103:2763.For a review of catalytically generated allylic metal reagents that serve as electrophiles, see: Lu Z, Ma S. Angew Chem Int Ed. 2008;47:258.

Publication types

LinkOut - more resources