3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT):: A new coupling reagent with remarkable resistance to racemization

被引:224
作者
Li, HT [1 ]
Jiang, XH
Ye, YH
Fan, CX
Romoff, T
Goodman, M
机构
[1] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA
[2] Peking Univ, Dept Chem, Beijing 100871, Peoples R China
关键词
D O I
10.1021/ol990573k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The new crystalline phosphate reagent 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DE PBT) mediates am ide bond format ion with a remarkable resistance to racemization. Comparative racemization studies were carried out and DEPBT proved to be superior to typical phosphonium and uronium coupling reagents. DEPBT is easily prepared and is exceedingly stable with a shelf life of months at room temperature. The advantageous properties of DEPBT render it a useful and unique addition to the arsenal of coupling reagents.
引用
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页码:91 / 93
页数:3
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