Efficient and convenient procedure for the synthesis of...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

Reexamination Certificate

active

07109345

ABSTRACT:
A novel and efficient alkylation procedure of B—H-1,3,2-oxazaborolidines derived from ephedrine and norephedrine has been established. Representative B-butyl- and B-methyl-1,3,2-oxazaborolidines were prepared in good yield and excellent purity by one pot treatment of the parent boraheterocyclic compound with the corresponding organolithium reagent and subsequent hydrolysis of the cyclic borohydride with anhydrous ammonium chloride.

REFERENCES:
patent: 6005133 (1999-12-01), Quallich
patent: 6020495 (2000-02-01), Sun et al.
patent: 6037505 (2000-03-01), Quallich
patent: 2002/0038053 (2002-03-01), Draper
Shinichi Itsuno, Koichi Ito, Akira Hirao and Seiichi Nakahama; Asymmetric Reduction of Aliphatic Ketones with The Reagent Prepared from (S)-(-)-2-Amino-3-methyl-1, 1-diphenylbutan-1-OI And Borane;J. Org. Chem.; 1984; pp. 555-557; School of Materials Science, Toyohashi, Japan; Department of Polymer Science, Tokyo, Japan.
Elias J. Corey and Christopher J. Helal; Reduction of Carbonyl Compounds with Chiral Oxazaborolidine Catalysts; A New Paradigm for Enantioselective Catalysis and a Powerful New Synthetic Metod;Angewandte Chemie; 1988; pp. 1986-2012; Germany.
Yoji Sakito, Yukio Yoneyoshi, and Gohfu Suzukamo; Asymmetric Reduction of Oxime Ethers, Distinction of Anti and Syn Isomers Leading to Enantiomeric Amines;Tetrahedron Letters, 1988; pp. 223-224; Great Britain.
N. N. Joshi, M. Srebnik, and Herbert C. Brown; Chiral Oxazaborolidines as Catalysts for the Enantioselective Addition of Diethyizinc to Aldehydes;Tetrahedron Letters; 1989; pp. 5551-5554; Great Britain.
John M. Brown and Guy C. Lloyd-James; Catalytic Asymmetric Hydroboration with Oxazaborolidines;Tetrahedron: Asymmetry; 1990; pp. 869-872; Great Britain.
Vinod K. Singh; Practical and Useful Methods for Enantioselective Reduction of Unsymmetrical Ketones;Review; Indian Institute of Technology; 1991; pp. 605-617; India.
Laurent Deloux and Morris Srebnik; Asymmetric Boron-Catalyzed Reactions;Chem. Rev.; 1992; pp. 763-784; University of Toledo, Ohio, USA.
Byung Tae Cho and Yu Sung Chun; Asymmetric Borane Reduction of Achiral Ketones Mediated by a Chiral Oxazaborolidine Derieved from (-)-Ephedrine;Tetrahedron: Asymmetry; 1992; pp. 1539-1542; Great Britain.
Sabine Wallbaum and Jürgen Martens; Asymmetric Syntheses with Chiral Oxazaborolidines;Tetrahedron: Asymmetry; 1992; pp. 1475-1504; Great Britain.
P. Y. Chavant and M. Vaultier; Preparation of some organo-bis (diisopropylamino) boranes and their Application to the Synthesis of Oxazaborolidines;Journal of Organometallic Chemistry; 1992; pp. 37-46; France.
D. J. Mathre, Andre S. Thompson, Alan W. Douglas, Karst Hoosteen, James D. Carroll, Edward G. Corely, and Edward J. J. Grabowski; A Practical Process for the Preparation of Hydro-1-methil-3,3-diphenyl-1H,3H-pyrrolo[1,2-c]-oxazaborole-borane. A Highly Enantioselective Stoichiometric and Catalyctic Reducing Agent;J. Org. Chem; 1993; pp. 2880-2888; New Jersey, USA.
John M. Brown, Guy C. Lloyd-Jones, and Timothy P. Layzell; Reversible Dimerisation of Ephedrine-derived Oxazaborolidines ; Tetrahedron: Asymmetry; 1993; pp. 2151-2154; Great Britain.
Masako Nakagawa, Tomohiko Kawate, Taro Kakikawa, Hideki Yamada, Teruaki Matsui, and Tohru Hino; Asymmetric Reductions of Imines and Ketones by Chiral Oxaborolidines;Tetrahedron: Asymmetry; 1993; pp. 1739-1748; Chiba University; Japan; Great Britain.
Ramon Berenguer, Jordi Garcia, and Jaume Vilarrasa; Selective Reduction of Ketones Catalysed by Oxazaborolidines Prepared from Phenylglycine;Tetrahedron: Asymmetry; 1994; pp. 165-168; University of Barcelona, Spain; Great Britain.
Vesa Nevalainen; Quantum Chemical Modeling of Chiral Catalysis. Part 16. On the Isomerism of Dimers of Chiral Oxazaborolidines used in the Catalytic Enantioselective Reduction of Ketones.;Tetrahedron: Asymmetry; 1994; pp. 387-394; University of Helsinki, Finland; Great Britain.
George J. Quallich, James F. Blake, and Teresa M. Woodall; Oxazaborolidines Structure and Enantioselectivity Relationships;J. Am. Chem. Soc.; 1994; pp. 8516-8525; USA.
Byung Tae Cho, Yu Sung Chun, Ch. Dauelsberg, Sabine Wallbaum, and Jürgen Martens; Catalytic Enantioselective Reactions. Part 2. A Comparison Study of Asymmetric Borane Reduction of Prochiral Ketones Catalyzed by Chiral Oxazaborolidines;Communications to the Editor; 1994; pp. 101-103; Germany.
Byung Tae Cho, Mi Hae Ryu, Yu Sung Chun, Ch. Dauelsberg, Sabine Wallbaum, and Jürgen Martens; A Direct Comparison Study of Asymmetric Borane Reduction of C=N Double Bond Mediated by Chiral Oxazaborolidines;Bull. Korean Chem. Soc., 1994: pp. 53-57; Republic of Korea/Germany.
E. J. Corey and Karlene A. Cimprich; Highly Enantioselective Alkynylation of Aldehydes Promoted by Chiral Oxazaborolidines;J. Am. Chem. Soc.; 1994; pp. 3151-3152; USA.
Claude Caze, Noureddine El Moualij, Philip Hodge, Christopher J. Lock, and Jianbiao Ma; Some Enantioselective Borane Reductions of Prochiral Ketones Catalysed by Polymer-supported Oxazaborolidines Bound via the Boron Atom;J..Chem. Soc. Perkin Trans.; 1995; pp. 345-349; France/United Kingdom.
Jordi Bach, Ramon Berenguer, Jordi Garcia, Teresa Loscertales, and Jaume Vilarrasa; Highly Enantioenriched Propargylic Alcohols by Oxazaborolidine-Mediated Reduction of Acetylenic Ketones;J. Org. Chem.; 1996; pp. 9021-9025; Spain/USA.
Ahmed F. Abdel-Magid; Reductions in Organic Synthesis. Recent Advances and Practical Applications; American Chemical Society; 1996; pp. 112-126; USA.
John T. Dougherty, Joseph R. Flisak, Jerome Hayes, Ivan Lantos, Li Liu, and Lynn Tucker; Asymmetric reduction of ketoxime ethers to optically active O-substituted hydroxylamines with reagents prepared from borane and chiral amino alcohols;Tetrahedron: Asymmetric; 1997; pp. 497-499; Great Britain.
Byung Tae Cho, and Yu Sung Chun; Facile Synthesis of Terminal 1,2-Diols with High Optical Purity via Oxazaborolidine-Catalyzed Asymmetric Borane Reduction;J. Org. Chem.; 1998; pp. 5280-5282; USA.
Alberto Rosendo Rico, Margarita Tlahuextl, Angelina Flores-Parra, Rosalinda Contreras; Addition reactions of protonic reagents to optically active 2-phenyl-1,3,2-oxazaborolidines;Journal of Organometallic Chemistry; 1998; pp. 122-128; México/USA.
Cristina Puigjaner, Anton Vidal-Ferran, Albert Moyano, Miquel A. Pericas, and Antoni Riera; A New Family of Modular Chiral Ligands for the Catalytic Enantioselective Resuction of Prochiral Ketones;J. Org. Chem., 1999; pp. 7902-7911; Spain/USA.
Evelyne Fontaine, Claudie Namane, Jerome Meneyrol, Michel Geslin, Laurence Serva, Eliane Roussey, Stephanie Tiessandie, Mohamed Maftouh, and Pierre Roger; Synthesis of optically-active benzylic amines; asymmetric reduction of ketoxime ethers with chiral oxazaborolidines;Tetrahedron: Asymmetry; 2001; pp. 2185-2189; France/USA.
Akira Hirao, Shinichi Itsuno, Seiichi Nakahama, Noboru Yamazaki; Asymmetric Reduction of Aromatic Ketones with Chiral Alkoxy-amine-borane Complexes;J.C.S. Chem. Comm; 1981; pp. 315-317; US.
Jean-Paul G. Seerden, Mike M.M. Boeren, Hans W. Scheeren; 1,3-Dipolar Cycloaddition Reactions of Nitrones with Alkyl Vinyl Ethers Catalyzed by Chiral Oxazaborlidines;Tetrahedron, vol. 53; 1997; pp. 11843-11852; US.
George J. Quallich, James F. Blake, Teresa M. Woodall; Diphenyloxazaborolidine for Enantioselective Reduction of Ketones;American Chemical; 1996; pp. 112-126; US.
Byung Tae Cho, Mi Hae Ryu; Asymmetric Borane Reduction of Ketoxime O-Trimethylsilyl Ethers Mediated by a Chiral 1,3,2-Oxazaborolidine Derived from (-),Ephedrine;Bull. Korean Chem. Soc.; 1994; pp. 191-192; US.
John M. Brown, Guy C. Lloyd-Jones; Vinylborane Formation in Rhodium-catalysed Hydroborations; Ligand-free Homogeneous Catalysis;J. Chem. Soc., Chem. Commun.; 1992; pp. ; US.
Byung Tae Cho, Yu Sung Chun; Catalytic Enantioselective Reactions. Part 10. Enantioselective Addition of Diethylzinc to Aldhydes Catalyzed by Chiral Oxazaborolidenes; Bull. Korean Chem. Soc.; 1996; pp. 1096-1098; US.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Efficient and convenient procedure for the synthesis of... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Efficient and convenient procedure for the synthesis of..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Efficient and convenient procedure for the synthesis of... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3591936

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.