Multicomponent reactions: Synthesis of spirocyclic tetrahydropyran derivatives by Prins cyclization

Multicomponent reactions: Synthesis of spirocyclic tetrahydropyran derivatives by Prins cyclization
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DOI:
10.3987/com-02-s(m)63
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发表时间:
2002-11-22
期刊:
影响因子:
0.6
通讯作者:
Schiltz, G
Schiltz, G
中科院分区:
化学4区
文献类型:
--
作者:
Ghosh, AK;Shin, D;Schiltz, G

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在非水条件下,用各种环酮、高烯丙醇、甲烷磺酸或对甲苯磺酸进行Prins环化反应,以较高的产率合成了取代螺环四氢吡喃甲磺酸酯和对甲苯磺酸酯。然后,可以使用有效的两步程序将由此产生的甲磺酸盐转化为相应的BOC保护胺。
Substituted spirocyclic tetrahydropyranyl mesylates and tosylates have been synthesized in good yields using a Prins-type cyclization of various cyclic ketones, a homoallylic alcohol and either methanesulfonic or p-toluenesulfonic acid under non-aqueous conditions. The mesylates thus produced could then be transformed into the corresponding Boc-protected amines using an efficient two step procedure.