Addressing the competition between intramolecular acyl and beta ring cleavage in β-lactones

Tetrahedron Letters

Volumn 38, Issue 13, 1997, Pages 2223-2226

  White, Dominique ^a   Zemribo, Ronald ^a   Mead, Keith T ^a  

^a MISSISSIPPI STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031592599     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00329-8     Document Type: Article

References (11)

1. 1. (a) Mead, K. T.; Samuel, B. Tetrahedron Lett. 1988, 29, 6573;
2. (b) Mead, K. T.; Yang, H.-L. J. Org. Chem. 1990, 55, 2991.
3. 2. (a) Zemribo, R.; Champ, M. S.; Romo, D. SynLett 1996, 278;
4. (b) Arrastia, I.; Lecea, B.; Cossio, F. P. Tetrahedron Lett. 1996, 37, 245.
5. 3. Mead, K. T.; Pillai, S. K. Tetrahedron Lett. 1993, 34, 6997.
6. 2-promoted cycloadditions at -60°C, both α- and β-chelation control was found to be at least 98% diastereoselective. See: Zemribo, R.; Romo, D., Tetrahedron Lett. 1995, 36, 4159.
7. +, 291.1238 found.
8. 2-promoted 2+2 cycloaddition of TMS-ketene to 2,4-dibenzyloxy butanal. See reference 4.
9. 2.
10. 2 resulted in a mixture of acids 9 (39%) and their corresponding benzyl esters (46%).
11. 3) δ 171.70, 138.81, 128.35, 127.55, 127.45, 71.27, 70.06, 68.84, 68.45, 51.56, 41.26, 37.27, 34.85, 21.80