Enantioselective Tandem <i>O</i>-Nitroso Aldol/Michael Reaction

Abstract

This communication presents studies that illustrated nitroso Diels-Alder adduct has been obtained in uniformly high enantioselectivity via a tandem nitroso aldol/Michael reaction using an amine catalyst. The regiochemical outcome of this construction is documented to be the opposite to that of the normal nitroso aldol reaction, which has been determined by X-ray analysis. The reaction of the enone with silver-BINAP catalyst has also been investigated in conjunction with the control of regiochemistry in a stepwise process.

References

Page 1

	Year	Citations
New Strategies for Organic Catalysis: The First Highly Enantioselective Organocatalytic Diels−Alder Reaction Kateri A. Ahrendt, Christopher J. Borths, David W. C. MacMillan Journal of the American Chemical Society Chemical EngineeringOrganic CatalysisEngineeringNovel OrganocatalystsAltmetric Attention Score	2000	1.6K
Catalytic Asymmetric Hetero-Diels–Alder Reactions of Carbonyl Compounds and Imines Karl Anker Jørgensen Angewandte Chemie International Edition Carbonyl CompoundsNovel OrganocatalystsEngineeringAlkene MetathesisOrganic Chemistry	2000	637
Size‐Dependent Magnetic Properties of Colloidal Mn<sub>3</sub>O<sub>4</sub> and MnO Nanoparticles Won Seok Seo, Hyong Hoon Jo, Kwangyeol Lee, Angewandte Chemie International Edition NanoparticlesMagnetic PropertiesEngineeringPolymer-based MagnetMagnetic Resonance	2004	502
Direct Proline‐Catalyzed Asymmetric α‐Aminoxylation of Ketones Yujiro Hayashi, Junichiro Yamaguchi, Tatsunobu Sumiya, Angewandte Chemie International Edition Oxygen SourceEngineeringBiochemistryNatural SciencesCatalytic Synthesis	2004	274
Catalytic Enantioselective Synthesis of α-Aminooxy and α-Hydroxy Ketone Using Nitrosobenzene Norie Momiyama, Hisashi Yamamoto Journal of the American Chemical Society	2003	253
Direct Catalytic Enantioselective α‐Aminoxylation of Ketones: A Stereoselective Synthesis of α‐Hydroxy and α,α′‐Dihydroxy Ketones Anders Bøgevig, Henrik Sundén, Armando Córdova Angewandte Chemie International Edition Proline-catalyzed ReactionsEngineeringNatural SciencesDiversity-oriented SynthesisSuch Compounds	2004	247
Vinylogous Mannich reactions: selectivity and synthetic utility Scott K. Bur, Stephen F. Martin Tetrahedron Vinylogous Mannich ReactionsOrganic ChemistryStereoselective SynthesisChemistrySynthetic Chemistry	2001	224
Chiral Copper Complexes of Phosphino Sulfenyl Ferrocenes as Efficient Catalysts for Enantioselective Formal Aza Diels−Alder Reactions of <i>N</i>-Sulfonyl Imines Olga Garcı́a Mancheño, Ramón Goméz Arrayás, Juan C. Carretero Journal of the American Chemical Society Chemical EngineeringEngineeringAlkene MetathesisRelated DienesOrganic Chemistry	2003	190
Chiral Templating of SilicaâLipid Lamellar Mesophase with Helical Tubular Architecture We thank the University of Bristol and EPSRC for financial support, and Dr. S. A. Davis and Dr. C. GÃ¶ltner for helpful discussions. Annela M. Seddon, Harish M. Patel, Sandra L. Burkett, Angewandte Chemie International Edition	2002	176
<i>O</i> -nitroso aldol synthesis: Catalytic enantioselective route to α-aminooxy carbonyl compounds via enamine intermediate Norie Momiyama, Hiromi Torii, Susumu Saito, Proceedings of the National Academy of Sciences Asymmetric CatalysisChemical EngineeringPyrrolidine EnamineEngineeringBiochemistry	2004	165

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