将无环β-烷氧基酮高度选择性还原为受保护的顺式-1,3-二醇。
Highly selective reduction of acyclic beta-alkoxy ketones to protected syn-1,3-diols.
作者信息
Cullen Aaron J, Sammakia Tarek
机构信息
Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215, USA.
出版信息
Org Lett. 2004 Sep 2;6(18):3143-5. doi: 10.1021/ol048801k.
PMID:15330608
Abstract
[reaction: see text] The conversion of 1-(2-methoxyethoxy)ethyl-protected beta-hydroxy ketones to syn-1,3-ethylidene acetals is effected by Et(3)SiH and SnCl(4). This reaction is proposed to proceed via a cyclic oxocarbenium ion intermediate and provides the products in yields that range from 69 to 94% and with diastereoselectivities that are >200:1.
摘要
[反应：见正文] 1-(2-甲氧基乙氧基)乙基保护的β-羟基酮转化为顺式-1,3-亚乙基缩醛是由三乙基硅烷和四氯化锡实现的。该反应被认为是通过环状氧鎓离子中间体进行的，产物收率在69%至94%之间，非对映选择性大于200:1。
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