Reversal of regioselection in the asymmetric aminohydroxylation of cinnamates

Tetrahedron Letters

Volumn 39, Issue 17, 1998, Pages 2507-2510

  Tao, Beata ^a   Schlingloff, Gunther ^a   Sharpless, K Barry ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Amino acids and derivatives; Amino alcohols; Asymmetric reactions; Catalysis

Indexed keywords

CINNAMIC ACID;

ARTICLE; CATALYSIS; DRUG HYDROXYLATION; DRUG SYNTHESIS; ENANTIOMER; STEREOCHEMISTRY;

EID: 0032560012     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00350-5     Document Type: Article

References (12)

1. 1. a) Kolb, H. C.; Sharpless, K. B. in 'Transition Metals for Fine Chemicals and Synthesis': Bolm, C; Beller, M. Eds.; VCH/Wiley, Weinheim, in print.
2. b) Schlingloff, G.; Sharpless, K. B. in 'Asymmetric Oxidation: A Practical Approach': Katsuki, T., Ed.; Oxford University Press, Oxford, in print.
3. 2. a) Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem. Int. Ed. Engl. 1996, 35, 451-454.
4. b) Rudolph, J.; Sennhenn, P. C.; Vlaar, C. P.; Sharpless, K. B. Angew. Chem. Int. Ed. Engl. 1996, 35, 2810-2813.
5. 3. Bruncko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem. Int. Ed. Engl. 1997, 36, 1483-1486.
6. 4. a) Li, G.; Angert, H. H.; Sharpless, K. B. Angew. Chem. Int. Ed. Engl. 1996, 35, 2813-2817.
7. b) Laxma Reddy, K.; Sharpless, K. B. J. Am. Chem. Soc. 1998, in press.
8. c) Laxma Reddy, K.; Dress, R.; Sharpless, K. B. manuscript in preparation.
9. nd edition, New York, 1991.
10. 6. Becker, H.; Sharpless, K. B. Angew. Chem. Int. Ed. Engl. 1996, 35, 448-451.
11. 7. All products were characterized by means of NMR, MS, melting point, optical rotation, and HPLC.
12. +: 352.1161, found: 352.1152; HPLC: Chiralcel OD-H, 0.46 cm × 25 cm, hexane/i-PrOH 85/15, 0.6 mL/min, 210 nm, 30.1 min (2R, 3S), 33.7 min (2S, 3R). The absolute configuration of this compound was determined by hydrogenolytic removal of the CBz-group, followed by comparison of the resulting aminohydroxyester's optical rotation with the literature value; T. Beulshausen, U. Groth, U. Schöllkopf, Liebigs Ann. Chem. 1991, 1207-1209.