Preparation of Chiral Multifunctional Thiourea-Phosphanes and Synthesis of Chiral Allylic Phosphites and Phosphane Oxides through Asymmetric Allylic Substitution Reactions of Morita-Baylis-Hillman Carbonates

被引:55
作者
Deng, Hong-Ping [1 ]
Shi, Min [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
Organocatalysis; Asymmetric catalysis; Allylic compounds; Amines; N-SULFONATED IMINES; METHYL VINYL KETONE; HILIMAN REACTION; ALPHA-AMINO; ENANTIOSELECTIVE CONSTRUCTION; BIFUNCTIONAL ORGANOCATALYSTS; GAMMA-BUTENOLIDES; BASE; ACID; PHOSPHINOTHIOUREA;
D O I
10.1002/ejoc.201101365
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We developed a synthetic method to prepare chiral multifunctional thiourea-phosphane catalysts for the asymmetric allylic substitution reaction of Morita-Baylis-Hillman carbonates with diphenyl phosphite or diphenylphosphane oxide to give allylic phosphites and allylic phosphane oxides in high yields with excellent enantioselectivity.
引用
收藏
页码:183 / 187
页数:5
相关论文
共 70 条
[1]  
[Anonymous], 2009, Angew. Chem. Int. Ed
[2]  
[Anonymous], CHEM COMMUN
[3]  
[Anonymous], ANGEW CHEM INT ED
[4]  
[Anonymous], 2010, ANGEW CHEM, DOI DOI 10.1002/ANGE.201000446
[5]   Mechanistic investigations of multidentate organocatalyst-promoted counterion catalysis for fast and enantioselective aza-Morita-Baylis-Hillman reactions at ambient temperature [J].
Anstiss, Christopher ;
Garnier, Jean-Marc ;
Liu, Fei .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (19) :4400-4407
[6]   Hydrophosphonylation of activated alkenes and alkynes via fluoride ion activation in ionic liquid medium [J].
Balaraman, E. ;
Srinivas, Venu ;
Swamy, K. C. Kumara .
TETRAHEDRON, 2009, 65 (36) :7603-7610
[7]  
Betti M., 1941, Org Synth Coll, V1, P381
[8]  
Betti M., 1906, Gazz. Chim. Ital, V36, P392
[9]  
Betti M., 1900, Gazz. Chim. Ital, VII, P301
[10]  
Betti M., 1900, Gazz. Chim. Ital, V30, P310