Radical reaction of the dimethacrylic ester of (2R,4R)-2,4-pentanediol. Addition-cyclization-termination process of high yield under rigorous stereocontrol of the termination step

Tetrahedron Letters

Volumn 38, Issue 20, 1997, Pages 3547-3548

  Sugimura, Takashi ^a   Nagano, Shinya ^a   Tai, Akira ^a  

^a UNIVERSITY OF HYOGO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DICARBOXYLIC ACID DERIVATIVE; LACTONE DERIVATIVE; MACROCYCLIC COMPOUND;

ARTICLE; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; IN VITRO STUDY; PHOTOLYSIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030977651     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00699-0     Document Type: Article

References (7)

1. For review, see, Stacy, F. W.; Harris, Jr., J. F., Organic reactions Vol. 13 (1963) John Wiley, New York, Ed. by Adams, R., pp. 150-376.
2. The two-steps yields under the other conditions were as follows; with 3.3 mM of 1 and 3.3 mM of thiophenol, 20.7%; with 1.1 mM of 1 and 1.1 mM of thiophenol, 42.2%; with 3.3 mM of 1 and 9.9 mM of thiophenol, 35.6% based on 1.
3. D = -8.5) because of the side processes of β-elimination of 7 and following Michael addition of 6 to the resulting methyl methacrylate.
4. 4 also did not result in the intramolecular cyclization.
5. Addition of lithium amide to the α,β-unsaturated dioic esters resulted in a tandem reaction consisting of Michael addition of amide and subsequent intramolecular addition of the resulting ester anion when the produced ring size was five or six. This reaction could not be applied for the substrate to construct a seven-membered ring. Uyehara, T.; Shida, N.; Yamamoto, Y., J. Chem. Soc., Chem. Commun., 1986, 113-114. See also, Saito, S.; Hirohara, Y.; Narahara, O.; Moriwake, T., J. Am. Chem. Soc., 1989, 111, 4533-4535.
6. Addition of lithium amide to the α,β-unsaturated dioic esters resulted in a tandem reaction consisting of Michael addition of amide and subsequent intramolecular addition of the resulting ester anion when the produced ring size was five or six. This reaction could not be applied for the substrate to construct a seven-membered ring. Uyehara, T.; Shida, N.; Yamamoto, Y., J. Chem. Soc., Chem. Commun., 1986, 113-114. See also, Saito, S.; Hirohara, Y.; Narahara, O.; Moriwake, T., J. Am. Chem. Soc., 1989, 111, 4533-4535.
7. Curran, D. P.; Porter, N. D.; Giese, B., Stereochemistry of Radical Reaction, VHC, Weinheim (1996) pp. 116-146.