3 years ago

Organocatalytic Asymmetric Allylic Alkylation of Morita–Baylis–Hillman Carbonates with Diethyl 2-Aminomalonate Assisted by In Situ Protection

Organocatalytic Asymmetric Allylic Alkylation of Morita–Baylis–Hillman Carbonates with Diethyl 2-Aminomalonate Assisted by In Situ Protection
Hua Yang, Jun-An Xiao, Jing Wang, Xiao-Qing Chen, Yu Zheng, Peng-Ju Xia, Qing-lan Zhao, Hao-Yue Xiang
With the aid of in situ protection by N-(2-formylphenyl)-4-methyl-benzenesulfonamide, enantioselective allylic alkylation of Morita–Baylis–Hillman carbonates with diethyl 2-aminomalonate was successfully realized. The corresponding adducts can be obtained in up to 99% yield with up to 98% ee as well as excellent regioselectivity. Besides, the adducts with opposite configurations were readily prepared by utilizing easily available and inexpensive quinine or quinidine as organocatalyst. Facile deprotection of the resulting adduct provides straightforward access to enantiopure α-methylene-γ-lactam.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02064

DOI: 10.1021/acs.joc.7b02064

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.