Title:
AUTOMATED SYNTHESIS OF SMALL MOLECULES USING CHIRAL, NON-RACEMIC BORONATES
Document Type and Number:
WIPO Patent Application WO/2012/149182
Kind Code:
A3
Abstract:
Provided are methods for making and using chiral, non-racemic protected organoboronic acids, including pinene-derived iminodiacetic acid (PIDA) boronates, to direct and enable stereoselective synthesis of organic molecules. Also provided are methods for purifying PIDA boronates from solution. Also provided are methods for deprotection of boronic acids from their PIDA ligands. The purification and deprotection methods may be used in conjunction with methods for coupling or otherwise reacting boronic acids. Iterative cycles of deprotection, coupling, and purification can be performed to synthesize chiral, non-racemic compounds. The methods are suitable for use in an automated chemical synthesis process. Also provided is an automated small molecule synthesizer apparatus for performing automated stereoselective synthesis of chiral, non-racemic small molecules using iterative cycles of deprotection, coupling, and purification.
Inventors:
BURKE MARTIN D (US)
LI JUNQI (US)
GILLIS ERIC P (US)
LI JUNQI (US)
GILLIS ERIC P (US)
Application Number:
PCT/US2012/035247
Publication Date:
January 24, 2013
Filing Date:
April 26, 2012
Export Citation:
Assignee:
UNIV ILLINOIS (US)
BURKE MARTIN D (US)
LI JUNQI (US)
GILLIS ERIC P (US)
BURKE MARTIN D (US)
LI JUNQI (US)
GILLIS ERIC P (US)
International Classes:
C07F5/02; C07C211/63; C08F212/36
Domestic Patent References:
| WO2012012756A1 | 2012-01-26 |
Foreign References:
| US20090030238A1 | 2009-01-29 | |||
| US20100121062A1 | 2010-05-13 |
Other References:
LI, J. ET AL.: "Pinene-Derived Iminodiacetic Acid(PIDA): A Powerful Ligand for Stereoselective Stnthesis and Iterative Cross-Coupling of C(sp3) Boronate Building Blocks.", J. AM. CHEM. SOC., vol. 133, 8 August 2011 (2011-08-08), pages 13774 - 13777
GILLIS, E. P. ET AL.: "A Simple and Modular Strategy for Small Molecule Synthesis: Iterative Suzuki-Miyaura Coupling of B-Protected Haloboronic Acid Building Blocks.", J. AM. CHEM. SOC., vol. 129, 2007, pages 6716 - 6717
GILLIS, E. P. ET AL.: "A Simple and Modular Strategy for Small Molecule Synthesis: Iterative Suzuki-Miyaura Coupling of B-Protected Haloboronic Acid Building Blocks.", J. AM. CHEM. SOC., vol. 129, 2007, pages 6716 - 6717
Attorney, Agent or Firm:
STEELE, ALan, W. et al. (Patent GroupSeaport West, 155 Seaport Boulevar, Boston MA, US)
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