N-chloro-N-sodio-2-trimethylsilyl ethyl carbamate: A new nitrogen source for the catalytic asymmetric aminohydroxylation

Tetrahedron Letters

Volumn 39, Issue 22, 1998, Pages 3667-3670

  Reddy, K Laxma ^a   Dress, K Ruprecht ^a   Sharpless, K Barry ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ENANTIOMER; ENZYME SUBSTRATE; HYDROXYLATION; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0032575177     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00644-3     Document Type: Article

References (11)

1. 1. (a) Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem. Int. Ed. Engl. 1996, 35, 451.
2. (b) Rudolph, J.; Sennhenn, P. C.; Vlaar, C. P.; Sharpless, K. B. Angew. Chem. Int. Ed. Engl. 1996, 35, 2831.
3. (c) Li, G.; Sharpless, K. B. Acta Chem. Scand. 1996, 50, 649.
4. 2. (a) Li, G.; Angert, H. H.; Sharpless, K. B. Angew. Chem. Int. Ed. Engl. 1996, 35, 2813.
5. (b) Reddy, K. L.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 1207.
6. 3. Bruncko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem. Int. Ed. Engl. 1997, 36, 1483.
7. 4. For the most recent experimental details for the carbamate-based AA process see Reddy, K. L.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 1207.
8. 5. TBAF in acetonitrile at 60 °C, 7 h. See also Carpino, L. A.; Tsao, J.-H.; Ringsdorf, H.; Fell, E.; Hettrich, G. J. J. Chem. Soc., Chem. Commun. 1978, 358, and Carpino, L. A.; Sau, A. C. J. Chem. Soc., Chem. Commun. 1979, 514.
9. 5. TBAF in acetonitrile at 60 °C, 7 h. See also Carpino, L. A.; Tsao, J.-H.; Ringsdorf, H.; Fell, E.; Hettrich, G. J. J. Chem. Soc., Chem. Commun. 1978, 358, and Carpino, L. A.; Sau, A. C. J. Chem. Soc., Chem. Commun. 1979, 514.
10. 6. The reaction will give a lower yield if the mixture is not homogeneous at this point. Sonication for ca. 5 min at RT may be required.
11. 4 in dilute NaOH should be used within 15 min after its preparation.