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

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.

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ACKNOWLEDGMENTS

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

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Chiral N-Acetyl Selone-Promoted Aldol Reactions

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Chiral N-Acetyl Selone-Promoted Aldol Reactions

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