Highly regio- and stereoselective four-component iodoamination of Se-substituted allenes.: an efficient synthesis of N-(3-organoseleno-2-iodo-2(Z)-propenyl) acetamides

被引:42
作者
Ma, SM [1 ]
Hao, XS
Huang, X
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
关键词
D O I
10.1039/b300879g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Z-Selectivity was observed for iodohydroxylation of Se-substituted allenes with I-2 and H2O, which is opposite to that of 1,2-allenyl sulfoxides. With n-hexane as the co-solvent Z-iodoamination leading to N-(3-organoseleno-2-iodo-2(Z)propenyl)acetamide was observed. A brief rational for the stereoselectivity of this reaction is provided.
引用
收藏
页码:1082 / 1083
页数:2
相关论文
共 35 条
[1]  
Aso M., 1995, TRENDS ORG CHEM, V5, P157
[2]  
BRANDSMA L, 1980, SYNTHESIS ACETYLENES
[3]  
Bruneau C., 1995, COMPREHENSIVE ORGANI, V1, P953
[4]  
GIUSEPPE C, 1984, J CHEM SOC P1, P255
[5]   Crystallographic characterisation of dihalogenodimethylselenium compounds, Me(2)SeX(2) (X=Cl, Br or I) and the dependence of their structures on the nature of the halogen [J].
Godfrey, SM ;
McAuliffe, CA ;
Pritchard, RG ;
Sarwar, S .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1997, (06) :1031-1035
[6]  
Hashmi ASK, 2000, ANGEW CHEM INT EDIT, V39, P3590
[7]  
LANDOR SR, 1982, CHEM ALLENES, V1
[8]  
LOWRY TH, 1987, MECH THEORY ORGANIC, P319
[9]   Reactions of electron-deficient alkynes and allenes under phosphine catalysis [J].
Lu, XY ;
Zhang, CM ;
Xu, ZR .
ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (07) :535-544
[10]  
MA S, 2002, ANGEW CHEM INT ED, V41