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
. 2013 Sep 6;15(17):4516-9.
doi: 10.1021/ol402081p. Epub 2013 Aug 15.

Dinuclear zinc-ProPhenol-catalyzed enantioselective α-hydroxyacetate aldol reaction with activated ester equivalents

Barry M Trost  1 , David J Michaelis, Mihai I Truica
Affiliations

Dinuclear zinc-ProPhenol-catalyzed enantioselective α-hydroxyacetate aldol reaction with activated ester equivalents

Barry M Trost et al. Org Lett. .

Abstract

An enantioselective α-hydroxyacetate aldol reaction that employs N-acetyl pyrroles as activated ester equivalents and generates syn 1,2-diols in good yield and diastereoselectivity is reported. This dinuclear zinc-ProPhenol-catalyzed transformation proceeds with high enantioselectivity with a wide variety of substrates including aryl, alyl, and alkenyl aldehydes. The resulting α,β-dihydroxy activated esters are versatile intermediates for the synthesis of a variety of carboxylic acid derivatives including amides, esters, and unsymmetrical ketones.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Variation of activated ester structure.
Scheme 1
Scheme 1
Hydroxyacetyl aldol in laulimalide synthesis.
Scheme 2
Scheme 2
Synthesis of N-(α-hydroxyacetyl)-2-ethylpyrrole.
Scheme 3
Scheme 3
Derivatization of N-acylpyrrole products.
Scheme 4
Scheme 4
Diol synthesis towards peloruside A.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Mukaiyama T, Shiina I, Uchiro H, Kobayashi S. Bull. Che. Soc. Jpn. 1994;67:1708–1716. (b) For a review of direct aldol reactions, which includes α-hydroxyacetate aldols, see: Trost BM, Brindle CS. Chem. Soc. Rev. 2010;39:1600–1632. (c) For a recent review on additions to imines, which includes α-hydroxycarbonyl enolate donors, see: Kobayashi S, Mori Y, Fossey JS, Salter MM. Chem. Rev. 2011;111:2626–2704.

    1. For selected reviews of osmium-catalyzed syn dihydroxylations, see: Tse MK, Schroeder K, Beller M. In: Modern Oxidation Methods. 2nd edition Bäckvall J-E, editor. Wiley-VCH; Weinheim: 2010. pp. 1–36. Zaitsev AB, Adolfsson H. Synthesis. 2006:1725–1756. Kolb HC, VanNieuwenhze MS, Sharpless KB. Chem. Rev. 1994;94:2483–2547.

    1. Yoshikawa N, Kumagai N, Matsunaga S, Moll G, Ohshima T, Suzuki T, Shibasaki M. J. Am. Chem. Soc. 2001;123:2466–2467. - PubMed
    2. Kumagai N, Matsunaga S, Kinoshita T, Harada S, Okada S, Sakamoto S, Yamaguchi K, Shibasaki M. J. Am. Chem. Soc. 2003;125:2169–2178. - PubMed
    3. Trost BM, Ito H, Silcoff ER. J. Am. Chem. Soc. 2001;123:3367–3368. - PubMed

    1. Notz W, List B. J. Am. Chem. Soc. 2000;122:7386–7387. For selected recent examples, see the following and references therein: Ma G, Bartoszewicz A, Ibrahem I, Córdova A. Adv. Synth. Catal. 2011;353:3114–3122. Wu C, Fu X, Li S. Tetrahedron: Asymmetry. 2011;22:1063–1073. Chen X-H, Luo S-W, Tang Z, Cun L-F, Mi A-Q, Jiang Y-Z, Gong L-Z. Chem. Eur. J. 2007;13:689–701. Ramasastry SSV, Zhang H, Tanaka F, Barbas CF., III J. Am. Chem. Soc. 2007;129:288–289.

    1. For an enantioselective direct aldol reaction with ester derivatives, see: Misaki T, Takimoto G, Sugimura T. J. Am. Chem. Soc. 2010;132:6286–6287. and references therein.

Publication types

LinkOut - more resources