Preparation and evaluation of a cyclic acyl nitrone as a synthon for stereospecific α-amino acid synthesis

Tetrahedron Letters

Volumn 39, Issue 38, 1998, Pages 6819-6822

  Baldwin, Steven W ^a   Young, Bruce G ^a   McPhail, Andrew T ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

Cycloadditions; Nitrones; Stereoselection; X ray crystal structures

Indexed keywords

ALPHA AMINO ACID;

AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0032541709     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01474-9     Document Type: Article

References (12)

1. 1. (a) Tufariello, J.; Puglis, J. Tetrahedron Lett. 1986, 27, 1265-1268.
2. (b) Black, D.; Crozier, R.; Davis V. Synthesis 1975, 205-221.
3. (c) Carruthers, W. Cycloaddition Reactions in Organic Synthesis Pergamon: New York, 1990.
4. (d) Padwa, A. Intermolecular 1,3-Dipolar Cycloadditions. In: Trost, B.M. ed. Comprehensive Organic Synthesis. New York, Pergamon, 1991: 4, 1069-1109.
5. 2. Williams, R.; Sinclair, P.; Zhai, D.; Chen, D. J. Am. Chem. Soc. 1988, 110, 1547-1557.
6. 3. Dellaria, J.; Santarsiero, B. J. Org. Chem. 1989, 54, 3916-3926.
7. 4. Williams, R. Aldrichimica Acta 1992, 25, 11-25.
8. 5. Anslow, A.; Harwood, L.; Phillips, H.; Watkin, D.; Wong, L. Tetrahedron Asymm. 1991, 2, 1343-1358.
9. 6. Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J.; Pater, R. J. Org. Chem. 1980, 45, 4758-4760.
10. 3 to which a phosphate/water buffer and a phase transfer catalyst have been added. Acetone is added to the mixture and then Oxone® added dropwise as an aqueous solution. The Oxone® oxidizes acetone to dimethyl dioxirane which is then consumed by its reaction with 1. Additional buffer is added periodically to keep the pH at a constant 7.5. The reaction takes approximately 1h per gram of amine, can be scaled to any size, and purification involves simple chloroform extraction. The reaction proceeds smoothly in good (70-80%) yield.
11. 13CNMR δ 175.4, 170.0, 130-132, 80.5, 73.9, 69.5, 62.9, 62.3, 55.9,21.3.
12. 9. Crystallographic data for 10, 12, and 13 have been deposited at the Cambridge Crystallographic Data Center.