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Asymmetric a-amino anions

The tetrahydroisoquinoline nucleus is found in literally thousands of alkaloids, many of which are of great medicinal importance. The tetrahydro-P-carboline nucleus is also widely distributed in the plant kingdom. Meyers has developed a valuable asynunetric synthesis of such systems which is based on an (5)-valine-derived chiral auxiliary, abbreviated to VBE.P7] [Pg.118]

The methylene group adjacent to the nitrogen can be metallated with strong base to give an a-amino anion in which the lithium cation is chelated by th two heteroatoms of the chiral auxiliary. It is interesting to compare the alternative route to chiral 2-alkylated tetrahydroisoquinolines described in section 6.4.1. [Pg.119]

The method works equally well with tetrahydro-j8-carbolines, as shown by the asymmetric synthesis of the alkaloid yohimbone. [Pg.119]


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A Anionic

A asymmetric

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