Novel 1,3-sulfonyl shift and [4+2] cycloaddition reaction of N-allenyl sulfonamide promoted by allylsilane

Tetrahedron Letters

Volumn 41, Issue 18, 2000, Pages 3427-3431

  Horino, Yoshikazu ^a   Kimura, Masanari ^a   Naito, Makoto ^a   Tanaka, Shuji ^a   Tamaru, Yoshinao ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

Allenes; Cycloadditions; Rearrangements; Silicon and compounds

Indexed keywords

OXAZOLIDINE DERIVATIVE; PYRIDINE DERIVATIVE; SILANE DERIVATIVE; SULFONAMIDE;

ARTICLE; REACTION ANALYSIS; SYNTHESIS;

EID: 0034728833     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00393-2     Document Type: Article

References (9)

1. Kimura, M.; Horino, Y.; Wakamiya, Y.; Okajima, T.; Tamaru,Y. J. Am. Chem. Soc. 1997, 119, 10869-10870.
2. Horino, Y.; Kimura, M.; Wakamiya, Y.; Okajima, T.; Tamaru, Y. Angew. Chem., Int. Ed. Engl. 1999, 38, 121-123.
3. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293.
4. Knolker, H.-J. J. Prakt. Chem. 1997, 339, 304-314. In most cases, these reactions are promoted only in the presence of some Lewis acid catalysts.
5. 4NSSi: C, 58.94; H, 7.17; N, 3.44; found: C, 58.57; H,7.03; N, 3.42.
6. The authors have deposited atomic coordinates for 5a and 6 (deposition nos. CCDC-139284/139285) with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre 23 Union Road, Cambridge, CB2 1EZ, UK.
7. (a) Mayr, H.; Patz, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 984-947.
8. (b) Burfeindt, J.; Patz, M.; Muller, M.; Mayr, H. J. Am. Chem. Soc. 1998, 120, 3629-3634.
9. (Z)-4h isomerized during the reaction and (Z)-4h/(E)-4h=3.7:1 was recovered from the reaction mixture.