Asymmetric grignard synthesis with cyclic 1,2 aminoalcohols

Chemistry: molecular biology and microbiology – Enzyme – proenzyme; compositions thereof; process for... – Hydrolase

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

548217, C07D26308

Patent

active

060251778

ABSTRACT:
Processes for preparing a single enantiomer of an .alpha.,.alpha.-disubstituted-.alpha.-hydroxy acetic acid, especially cyclohexylphenylglycolic acid (CHPGA), is disclosed. The processes employ cyclic 1,2-aminoalcohols as chiral auxiliaries by forming diastereomeric esters of aminoalcohols or diastereomeric amides of oxazolidines. ##STR1## Intermediates useful in the process are also disclosed.

REFERENCES:
patent: 5516943 (1996-05-01), Gao et al.
Hamon et al. "Asymmetric Syntheses with a new Optically Active..." Tetrahedron 42, 9593-9604 (1993).
Boireau et al. "Synthese D'.alpha.-Hydroxyacides Optiquement Actifs Par Addition..." Tetrahedron 45, 5837 (1989).
Basavaiah et al. "New Cyclohexyl-Based Chiral Auxiliaries: Enantioselective..."'Tetrahedron 51, 12169-78 (1995).
Boireau et al. "Application De Reactions D'Hydroalumination En Synthese... " Tetrahedron Letters 26, 4181-4182 (1985).
Boireau et al. "Addition Diastereoselective D'Organozinciques Sur Le..." Tetrahedron Letters 29, 215-2176 (1988).
Basavaiah et al. "Enantioselective Synthesis of .alpha.-and .beta.-Hydroxy Acids Using..." Tetrahedron Letters 32 , 3417-3420 (1991).
Tamai et al. "Reinvestigation of the Addition of Methylmagnesium Iodide to the..." Chemistry Letters , 1135-1136 (1989).
Kawanami et al. "Diastereoselective Addition of Organometallics to N-(.alpha.-Ketoacyl)-..." Chemistry Letters, 2063-2066 (1989).
Akiyama et al. "Diastereoselective Addition of Organometallics to .alpha.-Keto Esters Bearing..." Chemistry Letters, 447-450 (1992).
Ghosh et al. "Highly Stereoselective Reduction of .alpha.-Keto Esters: Utility of Cis-1-..." Tetrahedron Letters 6811-6814 (1995).
Basavaiah et al. "trans-2-Phenoxycylcohexan-1-OL as New Chiral Auxilary: Synthesis..." Synthetic Communications 22, 941-47 (1992).
Solladie-Cavallo et al. "Diastereoselective Reduction of an .alpha.-Keto-Ester Derived... " Tetrahedron: Asymmetry 2, 1165-1171 (1991).
Tamai et al. "Investigation of the Diastereoselectivity in the Addition of Organometallics... " J. Chem. Soc. Perkin Trans. 1, 439-445 (1994).
Esser et al. "trans-2-tert-Butylcyclohexanol, A simple Selectively Optimized... " Angew. Chem. Int. Ed. Engl. 31, 1190-92 (1992).
Senanayake et al. "Regio-and Stereocontrolled Syntheses of Cyclic Chiral cis-Amino... " Tetrahedron Letters 36, 7615-7618 (1995).
Armstrong et al. "Stereocontrolled Addition of Chiral, Non-Racemic Amide Homoenolates..." Tetrahedron Letters 44, 6599-6602 (1992).
Askin et al. "Highly Diastereoselective Alkylations of Chiral Amide Enolates: New Routes..." J. Org. Chem. 57, 2772-2773 (1992).

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

Asymmetric grignard synthesis with cyclic 1,2 aminoalcohols does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Asymmetric grignard synthesis with cyclic 1,2 aminoalcohols, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Asymmetric grignard synthesis with cyclic 1,2 aminoalcohols will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-1904984

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