Lithium/Ammonia Cleavage of the N-N Bond in N-(MethoxycarbonyI)- and N-Acetylhydrazines

Scott E. Denmark, Olivier Nicaise, James P. Edwards

Research output: Contribution to journalArticlepeer-review


The diastereoselective addition of organocerium reagents to L-proline-derived hydrazones 1 has recently been reported from these laboratories1(Scheme I). The reaction is compatible with a wide range of substrates (R1= Ph, PhCH2,PhCH2CH2, (E)-CH3CH=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 proceed in good yield (67-81%) and with high diastereoselectivity (>93:7 ds).

Original languageEnglish (US)
Pages (from-to)6219-6223
Number of pages5
JournalJournal of Organic Chemistry
Issue number25
StatePublished - Dec 1990

ASJC Scopus subject areas

  • Organic Chemistry


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