Stereoselectivity of electrophile-promoted oxacyclizations of 1,4-dihydroxy-5-alkenes to 3-hydroxytetrahydropyrans
Stereoselectivity of electrophile-promoted oxacyclizations of 1,4-dihydroxy-5-alkenes to 3-hydroxytetrahydropyrans
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DOI：
10.1016/j.tet.2013.04.138
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发表时间：
2013-09-09
期刊：
影响因子：
2.1
通讯作者：
Hurtak, Jessica A.
中科院分区：
文献类型：
--
作者：
McDonald, Frank E.;Ishida, Kento;Hurtak, Jessica A.
利用不同的烯烃取代方式和亲电试剂，系统地研究了1，4-二羟基-5-烯烃烯丙基羟基的立体诱导作用。对于2-取代的3-羟基四氢吡喃的赤型非对映异构体的形成，三氟乙酸汞促进的顺式-和（Z）-烯基二醇的环化通常给出最高的非对映选择性。对于相应的1，4-二羟基-5-炔，三氟甲磺酸汞催化的环化反应，然后三乙基硅烷还原提供了一个替代路线的euthro-非对映异构体。(C)2013爱思唯尔有限公司保留所有权利。
Stereoinduction from the allylic hydroxyl group of 1,4-dihydroxy-5-alkenes has been systematically explored with various alkene substitution patterns and electrophilic reagents. For formation of erythro-diastereomers of 2-substituted 3-hydroxytetrahydropyrans, mercuric trifluoroacetate-promoted cyclizations of cis- and (Z)-alkenyldiols generally give the highest diastereoselectivities. For the corresponding 1,4-dihydroxy-5-alkyne, mercuric triflate-catalyzed cyclization followed by triethylsilane reduction affords an alternative route to the euthro-diastereomer. (C) 2013 Elsevier Ltd. All rights reserved.