Communication

Catalytic Enantioselective Aldol-type Reaction of β-Ketosters with Acetals†

  1. Natsuko Umebayashi1,3,
  2. Yoshitaka Hamashima Dr.1,
  3. Daisuke Hashizume Dr.2,
  4. Mikiko Sodeoka Prof.1,3

Article first published online: 25 APR 2008

DOI: 10.1002/anie.200705344

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 47, Issue 22, pages 4196–4199, May 19, 2008

Additional Information

How to Cite

Umebayashi, N., Hamashima, Y., Hashizume, D. and Sodeoka, M. (2008), Catalytic Enantioselective Aldol-type Reaction of β-Ketosters with Acetals. Angewandte Chemie International Edition, 47: 4196–4199. doi: 10.1002/anie.200705344

Author Information

  1. 1

    Synthetic Organic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan, Fax: (+81) 48-467-9373

  2. 2

    Molecular Characterization Team, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan

  3. 3

    Graduate School of Science and Engineering, Saitama University, 255 Shimo-okubo, Sakura-ku, Saitama 338-8570, Japan

  1. †

    We thank Prof. Teiji Chihara of RIKEN for his generous support. This work was supported by a Grant-in-Aid for the Encouragement of Young Scientists (B) from JSPS (No. 18790005), a Grant-in-Aid for Scientific Research on Priority Areas from MEXT (No. 19028065, “Chemistry of Concerto Catalysis”), and Special Project Funding for Basic Science from RIKEN.

Publication History

  1. Issue published online: 9 MAY 2008
  2. Article first published online: 25 APR 2008
  3. Manuscript Revised: 9 MAR 2008
  4. Manuscript Received: 21 NOV 2007

Funded by

  • RIKEN
  • JSPS. Grant Number: 18790005
  • MEXT. Grant Number: 19028065

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Keywords:

  • β-ketoester;
  • acetal;
  • aldol reaction;
  • palladium;
  • platinum

Graphical Abstract

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Two activations, one catalyst: By using cationic Pd and Pt complexes, a catalytic enantioselective aldol-type reaction of β-ketoesters with acetals has been developed (see scheme). The formation of metal enolates occurs under acidic conditions to allow the use of acetals as electrophiles to give the desired aldol products in high diastereoseletivity and enantioselectivity.

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