Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
4 years ago

Organocatalytic Nucleophilic Addition of Hydrazones to Imines: Synthesis of Enantioenriched Vicinal Diamines

Organocatalytic Nucleophilic Addition of Hydrazones to Imines: Synthesis of Enantioenriched Vicinal Diamines
Yang Wang, Qian Wang, Jieping Zhu
In the presence of a catalytic amount of chiral phosphoric acid, nucleophilic addition of N-monosubstituted hydrazones to N-Boc imines affords differentially protected vicinal diamines in the form of β-amino N,N′-dialkyldiazenes in excellent yields with high chemo-, diastereo-, and enantioselectivity. This catalytic asymmetric aza-Mannich reaction represents the first example in which N-alkyl hydrazones serve as α-azo carbanion equivalents to provide vicinal diamines with control of the two contiguous stereocenters. The adducts are readily converted into the monoprotected or free diamines and derivatives thereof. Two of a kind: Reaction of N-tert-butyl hydrazones with N-Boc imines in the presence of a catalytic amount of chiral phosphoric acid affords the differentially protected vicinal diamines as β-amino N,N′-dialkyl diazenes in high yields with excellent diastereo- and enantioselectivity. The adduct is readily converted into other diamine derivatives of high synthetic value.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201702295

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