| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5221569 | Tetrahedron | 2010 | 8 Pages |
Abstract
The intramolecular trapping of allenyl/propargyl anions, generated from sulfonylallenes with the proper base, by a haloalkyl group or an aldehyde functionality was investigated. The treatment of 1-(Ï-iodoalkyl)-1-(phenylsulfonyl)allenes with TBAF or NaH in DMF efficiently produced the 1-alkynyl-1-(phenylsulfonyl)-substituted three- to seven-membered carbocycles. The allenyl/propargyl anions could also be intramolecularly trapped using a terminal aldehyde to stereoselectively afford the 2-alkynyl-2-(phenylsulfonyl)-substituted five- and six-membered cycloalkanols. The latter reaction could be performed using a catalytic amount of TBAF or DBU.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Shinji Kitagaki, Satoshi Teramoto, Yuu Ohta, Harumi Kobayashi, Mika Takabe, Chisato Mukai,