Strain-release amination

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Presentation transcript:

Strain-release amination by Ryan Gianatassio, Justin M. Lopchuk, Jie Wang, Chung-Mao Pan, Lara R. Malins, Liher Prieto, Thomas A. Brandt, Michael R. Collins, Gary M. Gallego, Neal W. Sach, Jillian E. Spangler, Huichin Zhu, Jinjiang Zhu, and Phil S. Baran Science Volume 351(6270):241-246 January 15, 2016 Published by AAAS

Fig. 1 Synthetic methods for incorporating small, strained ring systems. Synthetic methods for incorporating small, strained ring systems. (A) Revisiting the retrosynthetic disconnection of an important scaffold in medicinal chemistry, bicyclo[1.1.1]pentan-1-amine. (B) Strain-release amination: “any-stage” functionalization of lead compounds in drug discovery. Ryan Gianatassio et al. Science 2016;351:241-246 Published by AAAS

Fig. 2 “Propellerization” of amine-containing substrates. “Propellerization” of amine-containing substrates. Isolated yields are reported. (A) An improved synthesis of the known bicyclo[1.1.1]pentan-1-amine. (B) A general “propellerization” of amines enabled by strain-release reagents. (C) Substrate scope of amine-containing substrates. Ryan Gianatassio et al. Science 2016;351:241-246 Published by AAAS

Fig. 3 “Azetidinylation” of amine-containing substrates. “Azetidinylation” of amine-containing substrates. (A) A general “azetidinylation” of amines enabled by strain-release reagents. (B) Scope of amine-containing substrates. Ryan Gianatassio et al. Science 2016;351:241-246 Published by AAAS

Fig. 4 “Cyclobutylation” of amine-containing substrates. “Cyclobutylation” of amine-containing substrates. (A) A general “cyclobutylation” of amines with C7 enabled by strain-release reagents. (B) Substrate scope of amine-containing substrates. (C) Diversification of intermediate cyclobutylsulfone 76. (D) Installation of cyclopentane onto primary and secondary amines by strain-release amination. Ryan Gianatassio et al. Science 2016;351:241-246 Published by AAAS

Fig. 5 Use of reagent C as a chemoselective cysteine tag for peptide and protein labeling. Use of reagent C as a chemoselective cysteine tag for peptide and protein labeling. (A) Reaction of C7 with functionalized peptides 86 and 87. (B) HPLC chromatogram depicting rapid and clean conversion of 86 to cysteine-labeled product 88 after 1 hour. (C) Superior chemoselectivity of reagent C7 relative to maleimide 89 in the presence of cysteine-free peptide 87. (D) Reaction kinetics demonstrating the tunable functionalization of 86 with substituted arylsulfonyl bicyclobutane reagents. Ryan Gianatassio et al. Science 2016;351:241-246 Published by AAAS