Cyclofunctionalization of unsaturated alcohols, phenols, acids, and sulfonamides with 1-benzene-sulfinyl piperidine and trifluoromethanesulfonic anhydride

Heterocycles

Volumn 62, Issue , 2004, Pages 827-830

  Crich, David ^a   Surve, Bhushan ^a   Sannigrahi, Mousumi ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 BENZENESULFINYLPIPERIDINE; ALCOHOL DERIVATIVE; BENZENESULFINAMIDE; CARBOXYLIC ACID DERIVATIVE; ETHER DERIVATIVE; LACTONE DERIVATIVE; PHENOL DERIVATIVE; PIPERIDINE DERIVATIVE; SULFONAMIDE; SULFUR; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CYCLIZATION; OXIDATION; REDUCTION;

EID: 0347720663     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-03-S(P)45     Document Type: Article

References (8)

1. D. Crich and M. Smith, J. Am. Chem. Soc., 2001, 123, 9015.
2. BSP and TTBP are commercially available from Lakeview Synthesis.
3. TTBP is a convenient, crystalline, non hygroscopic equivalent of the more familiar tert-butylated pyridines: D. Crich, M. Smith, Q. Yao, and J. Picione, Synthesis, 2001, 323.
4. D. Crich and J. Picione, Synlett, 2003, 1257.
5. P. Brownbridge, J. Chem. Soc., Chem. Commun., 1987, 1280.
6. Arenesulfenamides are also reported to bring about the amidinosulfenylation of alkenes in the presence of nitriles and a catalytic quantity of triflic acid: P. Brownbridge, Tetrahedron Lett., 1984, 25, 3759.
7. A number of other S(II) electrophiles have been successfully used in related thioetherification and esterification processes, both intra and intermolecular. For reviews see: C. M. Rayner in Organosulfur Chemistry: Synthetic Aspects, ed. by P. Page, Academic Press, Inc., London, 1995, pp. 89-131 and references therein.
8. S. Töteberg-Kaulen and E. Steckhan, Tetrahedron, 1988, 44, 4389.