Communication

Rapid and Stereochemically Flexible Synthesis of Polypropionates: Super-Silyl-Governed Aldol Cascades†

  1. Patrick B. Brady1,
  2. Prof. Dr. Hisashi Yamamoto1,2,*

Article first published online: 17 JAN 2012

DOI: 10.1002/anie.201108325

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 8, pages 1942–1946, February 20, 2012

Additional Information

How to Cite

Brady, P. B. and Yamamoto, H. (2012), Rapid and Stereochemically Flexible Synthesis of Polypropionates: Super-Silyl-Governed Aldol Cascades. Angew. Chem. Int. Ed., 51: 1942–1946. doi: 10.1002/anie.201108325

Author Information

  1. 1

    Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637 (USA)

  2. 2

    Adjunct affiliation: Chemistry Department, King Abdulaziz University, Jeddah, 21589 (Saudi Arabia)

*Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637 (USA)

  1. †

    This work was supported by the NIH (P50 GM086 145-01). P.B.B. is grateful for support as a trainee of the NIH NIGMS Predoctoral Chemistry & Biology Interface Training Program (T32 GM087 20). We would like to thank Dr. Antoni Jurkiewicz, Dr. Ian Steele, and Dr. Jin Qin for their expertise in NMR spectroscopy, X-ray crystallography, and mass spectrometry, respectively.

Publication History

  1. Issue published online: 14 FEB 2012
  2. Article first published online: 17 JAN 2012
  3. Manuscript Received: 26 NOV 2011

Funded by

  • NIH. Grant Number: P50 GM086 145-01

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Keywords:

  • aldol reaction;
  • cascade reactions;
  • diastereoselectivity;
  • polyketides;
  • synthetic methods
Thumbnail image of graphical abstract

Polypropionates made EZ: The E/Z geometry of tris(trimethylsilyl)silyl super silyl enol ethers derived from propionaldehyde controls diastereoselectivity in the aldehyde crossed-aldol reaction. These silyl enol ethers can participate in polyaldol cascade reactions, thus allowing the one-pot synthesis of four different dipropionate stereotetrads (see scheme), and polyketides bearing up to five contiguous stereocenters.

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