The tert-butanesulfinyl group: An ideal chiral directing group and boc- surrogate for the asymmetric synthesis and applications of β-amino acids

Journal of Organic Chemistry

Volumn 64, Issue 1, 1999, Pages 12-13

  Tang, Tony P ^a   Ellman, Jonathan A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA AMINO ACID; SULFINAMIDE;

ARTICLE; CHIRALITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033534429     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9820824     Document Type: Article

References (17)

1. For a review of β-amino acid syntheses see: Cole, D. C. Tetrahedron 1994, 50, 9517-9582. For leading references on catalytic asymmetric syntheses of β-amino acids see: (a) Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431-432.
2. For a review of β-amino acid syntheses see: Cole, D. C. Tetrahedron 1994, 50, 9517-9582. For leading references on catalytic asymmetric syntheses of β-amino acids see: (a) Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431-432.
3. (b) Ishitani, H.; Ueno, M.; Kobayashi, S. Ibid. 1997, 119, 7153-7154.
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11. Acetate enolate additions to p-toluenesulfinyl aldimines have been explored by others: Davis, F. A.; Reddy, R. E.; Szewczyk, J. M. J. Org. Chem. 1995, 60, 7037-7039; Fujusawa, T.; Kooriyama, Y.; Shimizu, M. Tetrahedron Lett. 1996, 37, 3881-3884.
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14. 1H NMR.
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