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2. Stereoselective synthesis of anti-N-protected 3-amino-1,2-epoxides by nucleophilic addition to N-tert-butanesulfinyl imine of a glyceraldehyde synthon

Author

Harried, Scott S., Croghan, Michael D., Kaller, Matthew R., Lopez, Patricia, Wenge Zhong, Hungate, Randall, and Reider, Paul J.

Subjects
Nucleophilic reactions -- Usage, Amino compounds -- Chemical properties, Amino compounds -- Structure, Condensation -- Analysis, Epoxy compounds -- Chemical properties, Epoxy compounds -- Structure, Biological sciences, Chemistry
Abstract

The condensation of a di-O-TBS protected glyceraldehyde synthon with Ellman's reagent to form a bench-stable N-tert-butanesulfinyl imine 6 which served as a common intermediate for the stereoselective introduction of various R groups is reported. Two step elaboration of alcohols to both known and novel anti-N-protected-3-amino- 1,2-epoxides is also described.

Published
2009

3. An efficient and scalable one-pot double Michael addition-dieckmann condensation for the synthesis of 4,4-disubstituted cyclohexane [beta]-keto esters

Author

DeGraffenreid, Michael R., Bennett, Sarah, Caille, Sebastien, de Turiso, Felix Gonzalez-Lopez, Hungate, Randall W., Julian, Lisa D., Kaizerman, Jacob A., McMinn, Dustin L., Rew, Yosup, Daqing Sun, Xuelei Yan, and Powers, Jay P.

Subjects
Acetonitrile -- Chemical properties, Cyclohexane -- Chemical properties, Potassium compounds -- Chemical properties, Chemical synthesis -- Analysis, Biological sciences, Chemistry
Abstract

The preparation 4,4-disubstituted cyclohexane [beta]-keto esters from arylacetonitriles and arylacetates is described. The synthesis involved one-pot double Michael addition-Dieckmann condensation promoted by potassium tert-butoxide.

Published
2007

6. An Efficient and Scalable One-Pot Double Michael Addition-Dieckmann Condensation for the Synthesis of 4,4-Disubstituted Cyclohexane β-Keto Esters

Author

DeGraffenreid, Michael R., primary, Bennett, Sarah, additional, Caille, Sebastien, additional, Gonzalez-Lopez de Turiso, Felix, additional, Hungate, Randall W., additional, Julian, Lisa D., additional, Kaizerman, Jacob A., additional, McMinn, Dustin L., additional, Rew, Yosup, additional, Sun, Daqing, additional, Yan, Xuelei, additional, and Powers, Jay P., additional

Published
2007
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