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
. 2008 Jun 4;130(22):6922-3.
doi: 10.1021/ja8018934. Epub 2008 May 7.

Asymmetric petasis reactions catalyzed by chiral biphenols

Sha Lou  1 , Scott E Schaus
Affiliations

Asymmetric petasis reactions catalyzed by chiral biphenols

Sha Lou et al. J Am Chem Soc. .

Abstract

Chiral biphenols catalyze the enantioselective Petasis reaction of alkenyl boronates, secondary amines, and ethyl glyoxylate. The reaction requires the use of 15 mol % of (S)-VAPOL as the catalyst, alkenyl boronates as nucleophiles, ethyl glyoxylate as the aldehyde component, and 3 A molecular sieves as an additive. The chiral alpha-amino ester products are obtained in good yields (71-92%) and high enantiomeric ratios (89:11-98:2). Mechanistic investigations indicate single ligand exchange of acyclic boronate with VAPOL and tetracoordinate boronate intermediates.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Chiral Biphenols.
Scheme 1
Scheme 1
Scheme 2
Scheme 2
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Zhu J, Bienaymé H, editors. Multicomponent Reactions. Wiley-VCH: Weinheim; 2005.
    2. Yus M, Ramón DJ. Angew Chem Int Ed. 2005;44:1602–1634. - PubMed
    3. Dömling A. Chem Rev. 2006;106:17–89. - PubMed
    4. Guillena G, Ramón DJ, Yus M. Tetrahedron: Asymmetry. 2007;18:693–700.
    1. Petasis NA, Akritopoulou I. Tetrahedron Lett. 1993;34:583–586.
    2. Petasis NA, Zavialov IA. J Am Chem Soc. 1997;119:445–446.
    3. Petasis NA, Goodman A, Zavialov IA. Tetrahedron. 1997;53:16463–16470.
    4. Petasis NA, Zavialov IA. J Am Chem Soc. 1998;120:11798–11799.
    5. Petasis NA. Aust J Chem. 2007;60:795–798.
    1. Maruoka K, Ooi T. Chem Rev. 2003;103:3013–3028. - PubMed
    2. Ma JA. Angew Chem, Int Ed. 2003;42:4290–4299. - PubMed
    3. Najera C, Sansano JM. Chem Rev. 2007;107:4584–4671. - PubMed
    1. Harwood LM, Currie GS, Drew MGB, Luke RWA. Chem Commun. 1996:1953–1954.
    2. Koolmeister T, Södergren M, Scobie M. Tetrahedron Lett. 2002;43:5969–5970.
    3. Nanda KK, Trotter BW. Tetrahedron Lett. 2005;46:2025–2028.
    4. Southwood TJ, Curry MC, Hutton CA. Tetrahedron. 2006;62:236–242.
    1. Yamaoka Y, Miyabe H, Takemoto Y. J Am Chem Soc. 2007;129:6686–6687. - PubMed

Publication types