Steric hindrance-controlled Pd(0)-catalyzed coupling-cyclization of 2,3-allenamides and organic iodides.: An efficient synthesis of iminolactones and γ-hydroxy-γ-lactams

被引:63
作者
Ma, SM [1 ]
Xie, HX [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
关键词
D O I
10.1021/jo025967v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Under the catalysis of 1 mol % Pd(PPh3)(4), the reaction of 4,4-disubstituted 2,3-allenamides and organic iodides in toluene afforded iminolactones stereospecifically in >90% yields using K2CO3 (2 equiv)-5 mol % TBAB as the base. A similar reaction with 4-monosubstituted 2,3-allenamides afforded gamma-hydroxy-gamma-lactams in relatively lower yields. The N/O-attack selectivity may be determined by the steric effect at the 4-position of 2,3-allenamides.
引用
收藏
页码:6575 / 6578
页数:4
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