Synthesis of Enantiopure 1, 4??Dioxanes, Morpholines, and Piperazines from the Reaction of Chiral 1, 2??Diols, Amino Alcohols, and Diamines with Vinyl Selenones

…, C Scarponi, MG Rossi, L Testaferri…

Index: Bagnoli, Luana; Scarponi, Catalina; Rossi, Maria Giovanna; Testaferri, Lorenzo; Tiecco, Marcello Chemistry - A European Journal, 2011 , vol. 17, # 3 p. 993 - 999

Full Text: HTML

Citation Number: 32

Abstract

Abstract The reactions of readily available vinyl selenones with enantiopure 1, 2-diols, N- protected-1, 2-aminoalcohols, and diamines gave substituted enantiopure 1, 4-dioxanes, morpholines, and piperazines, respectively, in good to excellent yields. The same procedure was extended to the synthesis of thiomorpholine, benzodiazepine, and benzoxazepine. The reactions proceeded in one pot, in the presence of base, through a simple and novel ...

Related Articles:

Al2O3-supported Cu-catalyzed electrophilic substitution by PhSeBr in organoboranes, organosilanes, and organostannanes. A protocol for the synthesis of …

[Bhadra, Sukalyan; Saha, Amit; Ranu, Brindaban C. Journal of Organic Chemistry, 2010 , vol. 75, # 14 p. 4864 - 4867]

Formation of Cyclopropanes and Epoxides from Vinylselenonium Salts.

[Watanabe, Yoshihiko; Ueno, Yoshio; Toru, Takeshi Bulletin of the Chemical Society of Japan, 1993 , vol. 66, # 7 p. 2042 - 2047]

Mechanism of hydrolysis of aryl vinyl selenides. Selenium-stabilized carbonium ions

[McClelland, Robert M.; Leung, Michael Journal of Organic Chemistry, 1980 , vol. 45, # 1 p. 187 - 189]

Vinyl selenides and selenoxides: preparation, conversion to lithium reagents, Diels-Alder reactivity, and some comparisons with sulfur analogs

[Reich, Hans J.; Willis, William W.; Clark, Peter D. Journal of Organic Chemistry, 1981 , vol. 46, # 13 p. 2775 - 2784]

The reactions of lithiobisphenylselenomethane with chloromethyltrimethylsilane and iodomethyltrimethylstannane: Novel 1, 1-and 1, 2-elimination reactions in …

[Sarkar, Tarun K.; Satapathi, Tushar K. Tetrahedron Letters, 1989 , vol. 30, # 25 p. 3333 - 3334]

More Articles...