Syntheses of 1,2-Oxaphospholane 2-Oxides and 1,2-Oxaphosphole 2-Oxides

被引:5
|
作者
Xu, Jiaxi [1 ,2 ]
机构
[1] Beijing Univ Chem Technol, Coll Chem, Dept Organ Chem, State Key Lab Chem Resource Engn, 15 Northern 3rd Ring Rd East, Beijing 100029, Peoples R China
[2] Henan Agr Univ, Coll Sci, Zhengzhou, Peoples R China
来源
CHEMISTRYSELECT | 2023年 / 8卷 / 12期
基金
中国国家自然科学基金;
关键词
oxaphospholane; oxaphosphole; gamma-phosphonolactone; gamma-phosphinolactone; phostone; phostine; DIRECTED ORTHO-LITHIATION; X-RAY STRUCTURE; INTRAMOLECULAR CYCLOPROPANATION; PHOSPHORUS-HETEROCYCLES; EFFICIENT SYNTHESIS; PHOSPHOLIPASE-C; ACID; STEREOCHEMISTRY; DERIVATIVES; CYCLIZATION;
D O I
10.1002/slct.202300217
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
1,2-Oxaphospholane and 1,2-oxaphosphole 2-oxides, ?-phosphonolactones and ?-phosphinolactones, also called ?-phostones and ?-phostines, are important five-membered 1,2-oxaphosphaheterocycles and crucial motifs of some biologically active compounds. Various synthetic methods of these 1,2-oxaphosphaheterocycles have been developed till now. They can be divided as cyclization, annulation, cycloaddition, ring expansion and contractions. The cyclizations mainly include intramolecular nucleophilic substitution of 3-haloalkylphosphonic and phosphinic acid derivatives, esterification of 3-hydroxyalkylphosphonic/phosphinic acids, transesterification of alkyl 3-hydroxyalkylphosphonates/phosphinates, halocyclization of alkyl alk-2/3-enylphosphonates, halocyclization of allenylphosphonic acid derivatives, the transition metal-catalyzed oxidative cyclizations of benzyl/2-methylphenylphosphonic/phosphinic acids, and the Pd-catalyzed cyclization of ?-bromoalkyl phosphonates/phosphinates. The annulations covers [4+1] and [3+2] annulations. In this review, we have described various strategies and further development for the synthesis of 1,2-oxaphospholane and 1,2-oxaphosphole 2-oxides.
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页数:21
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