对烯丙醇的对映选择性二氯化。
Enantioselective dichlorination of allylic alcohols.
机构信息
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, California 92037, USA.
出版信息
J Am Chem Soc. 2011 Jun 1;133(21):8134-7. doi: 10.1021/ja202555m. Epub 2011 May 10.
Abstract
The development of an enantioselective allylic alcohol dichlorination catalyzed by dimeric cinchona alkaloid derivatives and employing aryl iododichlorides as chlorine sources is reported. Reaction optimization, exploration of the substrate scope, and a model for stereoinduction are presented.
摘要
报道了由二聚奎宁生物碱衍生物催化的对映选择性烯丙醇二氯化反应的发展，并采用芳基碘二氯化物作为氯源。反应优化、底物范围的探索以及立体诱导模型都被提出。
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2
Asymmetric total synthesis of (+)-danicalipin A.(+)-丹卡脂素 A 的不对称全合成。
Org Lett. 2011 Mar 4;13(5):908-11. doi: 10.1021/ol1029518. Epub 2011 Feb 2.
3
On the chlorenium source in the asymmetric chlorolactonization reaction.不对称氯内酯化反应中氯翁源的研究。
Org Lett. 2011 Feb 18;13(4):608-11. doi: 10.1021/ol102850m. Epub 2011 Jan 18.
4
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