Alkylthioether synthesis via imidazole mediated Mitsunobu condensation

Tetrahedron Letters

Volumn 40, Issue 15, 1999, Pages 2903-2906

  Falck, J R ^a   Lai, Jing Yu ^a   Cho, Su Dong ^a   Yu, Jurong ^a  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

Condensation; Intidazole; Mitsunobu; Thioethers

Indexed keywords

IMIDAZOLE; PHOSPHINE; SULFIDE;

ARTICLE; DRUG SYNTHESIS; DRUG TRANSFORMATION; ELECTRON TRANSPORT; FLUORINATION; POLYMERIZATION; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 0033537806     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00390-1     Document Type: Article

References (12)

1. Review: Hughes, D. L. Org. Reactions, 1992, 42, 335-656.
2. For example, see: Manna, S.; Falck, J. R.; Mioskowski, C. Syn. Comm. 1985, 15, 663-668.
3. Clive, D. L. J.; Kellner, D. Tetrahedron Lett. 1991, 32, 7159-7160.
4. Review: Hughes, D. L. Org. Prep. Proc. Intl. 1996, 28, 127-164.
5. Falck, J. R.; Yu, J. Tetrahedron Lett. 1992, 33, 6723-6726.
6. Falck, J. R.; Yu, J.; Cho, H.-S. Tetrahedron Lett. 1994, 35, 5997-6000.
7. For example, see: Yu, J.; Cho, H.-S.; Falck, J. R. J. Org. Chem. 1993, 58, 5892-5894.
8. Cf., Tanigawa, T.; Kanamaru, H.; Murahashi, S.-I. Tetrahedron Lett. 1975, 4655-4658.
9. 13C NMR: 30.97, 31.89, 35.67, 35.85, 117.86, 126.90, 129.37, 129.50, 135.43, 142.61.
10. Tsunoda, T.; Yamamiya, Y.; Itô, S. Tetrahedron Lett. 1993, 34, 1639-1642.
11. The utility of imidazole in mediating Mitsunobu condensations has been noted: Lai, J.-Y.; Yu, J.; Hawkins, R. D.; Falck, J. R. Tetrahedron Lett. 1995, 36, 5691-5694.
12. Modest yields of thioethers could be obtained from benzylic mercaptans in refluxing THF in the absence of imidazole.