Regio- and stereoselective hydrothiolation reactions of ynamides with diphenyldithiophosphinic acid: Straightforward synthesis of ketene N,S-acetal derivatives

Chemistry Letters

Volumn 37, Issue 1, 2008, Pages 40-41

  Yasui, Hiroto ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 38949141601     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2008.40     Document Type: Article

References (17)

1. For reviews on the chemistry of ynamides, see: a) C. A. Zificsak, J. A. Mulder, R. P. Hsung, C. Rameshkumar, L.-L. Wei, Tetrahedron 2001, 57, 7575.
2. b) J. A. Mulder, K. C. M. Kurtz, R. P. Hsung, Synlett 2003, 1379.
3. For Brønsted acid-catalyzed addition reaction of allyl or propargyl alcohol followed by Claisen rearrangement, see: a) J. A. Mulder, R. P. Hsung, M. O. Frederick, M. R. Tracey, C. A. Zificsak, Org. Lett. 2002, 4, 1383.
4. b) M. O. Frederick, R. P. Hsung, R. H. Lambeth, J. A. Mulder, M. P. Tracey, Org. Lett. 2003, 5, 2663.
5. For hydrohalogenation, see: c) J. A. Mulder, K. C. M. Kurtz, R. P. Hsung, H. Coverdale, M. O. Frederick, L. Shen, C. A. Zificsak, Org. Lett. 2003, 5, 1547.
6. For Brønsted acid-catalyzed hydroarylaion, see: d) Y. Zhang, Tetrahedron Lett. 2005, 46, 6483.
7. e) Y. Zhang, R. P. Hsung, X. Zhang, J. Huang, B. W. Slafer, A. Davis, Org. Lett. 2005, 7, 1047.
8. For Lewis acid-catalyzed reaction with carbonyl compounds, see: f) K. C. M. Kurtz, R. P. Hsung, Y. Zhang, Org. Lett. 2006, 8, 231.
9. g) L. You, Z. F. Al-Rashid, R. Figueroa, S. K. Ghosh, G. Li, T. Lu, R. P. Hsung, Synlett 2007, 1656.
10. 3. W. A. Higgins, P. W. Vogel, W. G. Craig, J. Am. Chem. Soc. 1955, 77, 1864.
11. Determined based on nuclear Overhauser effect. Syn addition reactions to ynamides under Brønsted acid catalysis was reported in Ref. 2d. (Chemical Equation Presented)
12. Hydrothiolation with aromatic dithiocarbonic acid could not be performed due to difficulty in preparing and purifying dithiocarbonic acid.
13. 2P(=S)SH, in 80% alcohol) = 2.6: a) M. I. Kabachnik, T. A. Mastrukova, A. E. Shipov, T. A. Melentyeva, Tetrahedron 1960, 9, 10.
14. a (PhSH, in DMSO) = 9.8: b) J. Courtot-Coupez, M. Le Démézet, Bull. Soc. Chim. Fr. 1969, 1033.
15. Keteniminium intermediates were also proposed in Ref. 2.
16. 2PLi in situ.
17. 31P NMR yield. It is not clear the reason why 4.0 equimolar amounts of t-BuLi were needed.