Di-functionalization of alkenes using an oxidant generated from manganese(II) chloride under oxygen: Synthesis of γ-lactones

Heterocycles

Volumn 47, Issue 1, 1998, Pages 97-100

  Hojo, Makoto ^a   Murakami, Chikara ^a   Ohno, Kaori ^a   Kuboyama, Jun ^a   Nakamura, Shin Ya ^a   Ito, Hajime ^a   Hosomi, Akira ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 18744403466     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-97-s(n)30     Document Type: Article

References (18)

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6. with HCl and NCS, C. H. Robinson, L. Finckenor, E. P. Oliveto, and D. Gould, J. Am. Chem. Soc., 1959, 81, 2191;
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11. I. E. Markó and P. F. Richardson, Tetrahedron Lett., 1991, 32, 1831;
12. P. F. Richardson and I. E. Markó, Synlett, 1991, 733.
13. The stereochemistry of the product was determined in comparison with the authentic samples for syn- and anti-isomers that were independently prepared according to ref. 7 and ref. 4, respectively.
14. W. A. Nugent, Tetrahedron Lett., 1978, 3427.
15. 2 and 12 equiv of LiOMe were employed.
16. For the chlorolactonization, see e.g. D. G. Garratt, M. D. Ryan, and P. L. Beaulieu, J. Org. Chem, 1980, 45, 839;
17. Y. Tamara, M. Mizutani, Y. Furukawa, S. Kawamura, Z. Yoshida, K. Yanagi, and M. Minobe, J. Am. Chem. Soc., 1984, 106, 1079.
18. Without the addition of cone. HCl, the starting alkene was recovered.