ASYMMETRIC TRANS-ADDITION REACTIONS USING CHIRAL SELENOBINAPHTHYLS
Asymmetric trans-addition reactions of (E)-phenylpropene, a mechanistically novel reaction, have been achieved by using chiral selenium-containing binaphthyl derivatives.Introduction of an amide group at 2'-position in the binaphthyl skeleton enhances considerably the diastereomeric excess (d.e.) of the asymmetric reaction presumably due to attractive interaction between the nitrogen lone pair and the seleniranium intermediate.Introduction of another chiral center in the amide group further enhances the d.e. as high as 79 percent, which is the highest asymmetric induction ever achieved in the asymmetric trans-addition reaction.
Tomoda, Shuji,Fujita, Ken-Ichi,Iwaoka, Michio
p. 247 - 252
(2007/10/02)
Double Differentiation in Asymmetric Methoxyselenenylation of trans-β-Methylstyrene
The effect of double differentiation in the reaction between chirally modified optically active di(2'-N-substituted amido-2-binaphthyl) diselenide and trans-β-methylstyrene has been examined.
Tomoda, Shuji,Fujita, Ken-ichi,Iwaoka, Michio
p. 129 - 131
(2007/10/02)
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