Synthesis of oxathiane and morpholine from acyclic precursors: a modified Mitsunobu reaction

被引：8
|
作者：
Paul, Nidhin [1 ]
Kaladevi, Selvam [1 ]
Beneto, Arockiam Jesin [1 ]
Muthusubramanian, Shanmugam [1 ]
Bhuvanesh, Nattamai [2 ]
机构：
[1] Madurai Kamaraj Univ, Sch Chem, Dept Organ Chem, Madurai 625021, Tamil Nadu, India
[2] Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA
来源：
TETRAHEDRON | 2012年 / 68卷 / 34期
关键词：
ENANTIOSELECTIVE SYNTHESIS; NAZAROV CYCLIZATION; ORGANOSULFUR COMPOUNDS; ALLYLIC SUBSTITUTION; EFFICIENT SYNTHESIS; GLYCOSYL DONORS; SULFONIUM IONS; DERIVATIVES; ANALOGS; 1,4-OXATHIANES;
D O I：
10.1016/j.tet.2012.06.029
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Synthesis of a set of isomeric 2,4,6-triarylmorpholines and 2,6-diaryloxathianes from the corresponding 1,5-diols has been described. The method provides an efficient route to six-membered heterocycles from acyclic diols and is found to be better than Mitsunobu procedure in yield and waste management. In a related study, the ring contraction of pyranone to two isomeric cyclopentenone derivatives through Nazarov reaction has been noticed. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6892 / 6901
页数：10
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