期刊
TETRAHEDRON
卷 66, 期 21, 页码 3687-3694出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.03.071
关键词
Allenyl anion; Propargyl anion; Ring-closing reaction; Cycloalkane
资金
- Grants-in-Aid for Scientific Research [21590008, 21590007] Funding Source: KAKEN
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-(omega-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. (C) 2010 Elsevier Ltd. All rights reserved.
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