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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 4
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Original Articles

Chiral N-Acetyl Selone-Promoted Aldol Reactions

Louis A. Silks III National Stable Isotope Resource, Bioenergy and Environmental Sciences Group (B8), Los Alamos National Laboratory, Los Alamos, New Mexico, USACorrespondence[email protected]
,
David B. Kimball Advanced Measurement Science Group (B9), Bioscience Division, Los Alamos National Laboratory, Los Alamos, New Mexico, USA
,
Duane Hatch National Stable Isotope Resource, Bioenergy and Environmental Sciences Group (B8), Los Alamos National Laboratory, Los Alamos, New Mexico, USA
,
Morgane Ollivault-Shiflett National Stable Isotope Resource, Bioenergy and Environmental Sciences Group (B8), Los Alamos National Laboratory, Los Alamos, New Mexico, USA
,
Ryszard Michalczyk National Stable Isotope Resource, Bioenergy and Environmental Sciences Group (B8), Los Alamos National Laboratory, Los Alamos, New Mexico, USA
&
Eddie Moody NMT Division, Los Alamos National Laboratory, Bioscience Division, Los Alamos, New Mexico, USA
Pages 641-653 | Received 19 Jun 2008, Published online: 28 Jan 2009
 
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Abstract

The chiral oxazolidineselone functionality was found to be an excellent partner in the stereospecific acetate aldol reaction with aldehydes via the titanium enolates. Good stereocontrol was obtained as determined by NMR spectroscopy. The oxazolidineselone also provided a straightforward way to establish the stereopurity of the coupling reaction through 77Se NMR spectroscopy.

ACKNOWLEDGMENTS

We thank the LANL LDRD program (X9DN) and the CDC for partial support for this work.

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