期刊论文详细信息
Molecules
Unusual Regioselectivity in the Opening of Epoxides by Carboxylic Acid Enediolates
Luis R. Domingo2  Salvador Gil2  Margarita Parra1 
[1] Department of Organic Chemistry, Universitat de València, Dr. Moliner 50, 46100 Burjassot, Spain. Fax +34(9)63543831; E-mails
关键词: Lactones;    lithium chloride;    nucleophilic addition;    regioselectivity;    diastereoselectivity;   
DOI  :  10.3390/molecules13061303
来源: mdpi
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【 摘 要 】

Addition of carboxylic acid dianions appears to be a potential alternative to the use of aluminium enolates for nucleophilic ring opening of epoxides. These conditions require the use of a sub-stoichiometric amount of amine (10% mol) for dianion generation and the previous activation of the epoxide with LiCl. Yields are good, with high regioselectivity, but the use of styrene oxide led, unexpectedly, to a mixture resulting from the attack on both the primary and secondary carbon atoms. Generally, a low diastereoselectivity is seen on attack at the primary center, however only one diastereoisomer was obtained from attack to the secondary carbon of the styrene oxide.

【 授权许可】

CC BY   
© 2008 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland.

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