Stereocontrolled Mukaiyama-type Aldol Reaction of Siloxypyrroles Derived from (S)-Glutamic Acid

Synlett

Volumn 1997, Issue 4, 1997, Pages 390-392

  Uno, Hidemitsu ^a,b   Baldwin, Jack E ^a   Churcher, Ian ^a   Russell, Andrew T ^a,c  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b EHIME UNIVERSITY   (Japan)

^c UNIVERSITY OF SALFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003139983     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-798     Document Type: Article

References (18)

1. Heathcock, C. H. Vol. Ed. Comprehensive Organic Synthesis Vol. 2; Trost, B. M.; Fleming, I. Eds; Pergamon Press (1991).
2. Mukaiyama, T. In Organic Reactions Vol. 28; p 203; John Wiley & Sons (1982).
3. Uno, H.; Baldwin, J. E.; Russell, A. T. J. Am. Chem. Soc., 1994, 116, 2139.
4. (a) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L. J. Org. Chem., 1992, 57, 3760;
5. (b) Rassu, G.; Casiraghi, G.; Spanu, P.; Pinna, L.; Fava, G. G.; Ferrari, M. B.; Pelosi, G. Tetrahedron: Asymmetry, 1992, 3, 1035;
6. Casiraghi, G.; Rassu, G. Synthesis, 1995, 607.
7. (a) Thottathil, J. K.; Moniot, J. L.; Mueller, R. H.; Wong, M. K. Y.; Kissick, T. P. J. Org. Chem., 1986, 51, 3140;
8. (b) Hamada, Y.; Kawai, A.; Kohno, Y.; Hara, O.; Shioiri, T. J. Am. Chem. Soc., 1989, 111, 1524.
9. 2O (0.5 ml) and pyridine (1 ml) overnight.
10. The X-ray analysis was carried out by Dr Alison Edwards, Chemical Crystallography Laboratory, University of Oxford, 9 Parks Road, Oxford OX1 3PD, UK. Present address: School of Chemistry, University of Melbourne, Parkeville, Victoria 3052, Australia.
11. Products resulting from Friedel Crafts processes were also isolated and will be discussed elsewhere.
12. MM2 as implemented in Macromodel 3.0 kindly supplied by Prof. W. C. Still (Columbia).
13. Harding, K. E.; Coleman, M. T.; Liu, L. T. Tetrahedron Lett., 1991, 31, 3795.
14. McIntosh, M. C.; Weinreb, S. M. J. Org. Chem., 1991, 56, 5010 and references cited therein.
15. Baussanne, I.; Rover, J. Tetrahedron Lett., 1996, 37, 1213.
16. Corey, E. J.; Choi, S. Tetrahedron Lett., 1993, 34, 6969; Corey, E. J.; Reichard, G. A. Tetrahedron Lett., 1993, 34, 6973; Fenteany, G.; Standaert, R. F.; Reichard, G. A.; Corey, E. J.; Schreiber, S. L. Proc. Natl. Acad. Sci. USA, 1994, 91, 3358.
17. Corey, E. J.; Choi, S. Tetrahedron Lett., 1993, 34, 6969; Corey, E. J.; Reichard, G. A. Tetrahedron Lett., 1993, 34, 6973; Fenteany, G.; Standaert, R. F.; Reichard, G. A.; Corey, E. J.; Schreiber, S. L. Proc. Natl. Acad. Sci. USA, 1994, 91, 3358.
18. Corey, E. J.; Choi, S. Tetrahedron Lett., 1993, 34, 6969; Corey, E. J.; Reichard, G. A. Tetrahedron Lett., 1993, 34, 6973; Fenteany, G.; Standaert, R. F.; Reichard, G. A.; Corey, E. J.; Schreiber, S. L. Proc. Natl. Acad. Sci. USA, 1994, 91, 3358.