3 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

You might also like
Discover & Discuss Important Research

Keeping up-to-date with research can feel impossible, with papers being published faster than you'll ever be able to read them. That's where Researcher comes in: we're simplifying discovery and making important discussions happen. With over 19,000 sources, including peer-reviewed journals, preprints, blogs, universities, podcasts and Live events across 10 research areas, you'll never miss what's important to you. It's like social media, but better. Oh, and we should mention - it's free.

  • Download from Google Play
  • Download from App Store
  • Download from AppInChina

Researcher displays publicly available abstracts and doesn’t host any full article content. If the content is open access, we will direct clicks from the abstracts to the publisher website and display the PDF copy on our platform. Clicks to view the full text will be directed to the publisher website, where only users with subscriptions or access through their institution are able to view the full article.