Concepedia

Asymmetric Synthesis of Highly Substituted β-Nitro Alcohols and Enantiomerically Enriched 4,4,5-Trisubstituted Oxazolidinones

David Crich, Krishnakumar Ranganathan, Sochanchingwung Rumthao, Michio Shirai

The Journal of Organic Chemistry · 2003 · 22 citations · 21 references

DOI

Concepts

Abstract

It is demonstrated that alpha,alpha-disubstituted-alpha-nitroketones are reduced to the corresponding trisubstituted nitro alcohols in good to excellent yield and enantiomeric excess by borane-dimethyl sulfide in the presence of a chiral oxazaborolidine catalyst. Reduction of the nitro alcohols to the corresponding amino alcohols and their subsequent conversion to enantiomerically enriched 4,4,5-trisubstituted oxazoldinones is also reported.

References

21

Synthesis and Antibacterial Activity of U-100592 and U-100766, Two Oxazolidinone Antibacterial Agents for the Potential Treatment of Multidrug-Resistant Gram-Positive Bacterial Infections

Steven J. Brickner, Douglas K. Hutchinson, Michael R. Barbachyn et al. · Journal of Medicinal Chemistry · 1996 · 573 citations

, , +16

A Dinuclear Zn Catalyst for the Asymmetric Nitroaldol (Henry) Reaction We thank the National Science Foundation and the National Institutes of Health, General Medical Sciences, for their generous support of our programs. Mass spectra were provided by the Mass Spectrometry Facility of the University of California, San Francisco, supported by the NIH Division of Research Resources.

Barry M. Trost, Vince S. C. Yeh · Angewandte Chemie International Edition · 2002 · 338 citations

, , +10

re- andsi-Face-Selective Nitroaldol Reactions Catalyzed by a Rigid Chiral Quaternary Ammonium Salt: A Highly Stereoselective Synthesis of the HIV Protease Inhibitor Amprenavir (Vertex 478)

E. J. Corey, Fuyao Zhang · Angewandte Chemie International Edition · 1999 · 294 citations

, , +13

Effect of Ligand Structure on the Zinc-Catalyzed Henry Reaction. Asymmetric Syntheses of (−)-Denopamine and (−)-Arbutamine

Barry M. Trost, Vince S. C. Yeh, Hisanako Ito et al. · Organic Letters · 2002 · 265 citations

, , +17

Efficient Diastereoselective and Enantioselective Nitroaldol Reactions from Prochiral Starting Materials: Utilization of La-Li-6,6'-Disubstituted BINOL Complexes as Asymmetric Catalysts

Hiroaki Sasai, Teruhisa Tokunaga, Shizue Watanabe et al. · The Journal of Organic Chemistry · 1995 · 252 citations

, , +11