Efficient enantio- and diastereoselective synthesis of enantiopure syn-α-bromo-β-hydroxy-α-methylpropionate esters and their cis-α,β-epoxy derivatives based on a chiral oxazaborolidinone-promoted asymmetric aldol reaction

Tetrahedron Asymmetry

Volumn 11, Issue 7, 2000, Pages 1537-1542

  Kiyooka, Syun Ichi ^a   Shahid, Kazi A ^a  

^a KOCHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 BROMO 3 HYDROXY 3 METHYLPROPIONIC ACID DERIVATIVE; HYDRACRYLIC ACID DERIVATIVE; OXAZABOROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034108383     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00089-6     Document Type: Article

References (12)

1. (a) Corey, E. J.; Choi, S. Tetrahedron Lett. 1991, 32, 2857-2860.
2. (b) Corey, E. J.; Lee, D.-H.; Choi, S. Tetrahedron Lett. 1992, 33, 6735-6738.
3. (c) Wang, Y.-C.; Su, D.-W.; Lin, C.-M.; Tseng, H.-L.; Li, C.-L.; Yan, T.-H. Tetrahedron Lett. 1999, 40, 3577-3580.
4. (d) Wang, Y. C.; Li, C.-L.; Tseng, H.-L.; Chuang, S.-C.; Yan, T. H. Tetrahedron: Asymmetry 1999, 10, 3249-3251.
5. As few examples have dealt with a quaternary carbon at the α-position, an enantioselective synthesis of α-bromo-α-fluoro-β-hydroxy esters has been reported from the standpoint of fluorine chemistry on biological activity: Iseki, K.; Kuroki, Y.; Kobayashi, Y. Synlett 1998, 437-439.
6. (a) Ohfune, Y.; Horikawa, M. J. Synth. Org. Chem. Jpn. 1997, 55, 982-993 and references cited therein.
7. (b) Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon Press: London, 1989.
8. (a) Kiyooka, S.-i. Rev. Heteroatom Chem. 1997, 17, 245-270.
9. (b) Kiyooka, S.-i.; Hena, M. A. J. Org. Chem. 1999, 64, 5511-5523.
10. Gawley, R. E.; Aubé, J. Principles of Asymmetric Synthesis; Pergamon: Amsterdam, 1996.
11. Kiyooka, S.-i.; Shahid, K. A.; Hena, M. A. Tetrahedron Lett. 1999, 40, 6447-6449.
12. Pauling, L. The Nature of the Chemical Bond, 3rd ed.; Cornell University Press, 1960; p. 260.