Lithium/ammonia cleavage of the nitrogen-nitrogen bond in N-(methoxycarbonyl)-and N-acetylhydrazines

SE Denmark, O Nicaise…

Index: Denmark, Scott E.; Nicaise, Olivier; Edwards, James P. Journal of Organic Chemistry, 1990 , vol. 55, # 25 p. 6219 - 6223

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Citation Number: 85

Abstract

The diastereoselective addition of organocerium reagents to L-proline-derived hydrazones 1 has recently been reported from these laboratories'(Scheme I). The reaction is compatible with a wide range of substrates (R'= Ph, PhCH2, PhCH2CH2,(E)-CH, CH= CH) and accommodates a variety of unstabilized nucleophiles (R3= Me, n-Bu, i-Pr, t-Bu, Ph, i- Pr3SiCH= CH) derived from either lithium or halomagnesium precursors. The additions ...