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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Modular and Stereoselective Synthesis of Cyclobutane β-Amino Alcohols
Xinyu Yang1, Tomoya Ozaki1, Bo Li1
1Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts, USA.
Abstract:
Cyclobutane β-amino alcohols are valuable structural motifs, yet their development has lagged behind that of five- and six-membered analogs due to limited synthetic accessibility. In this work, we report a general and modular strategy for the synthesis of diversely substituted cyclobutane β-amino alcohols. The electronic structure of 1,2-azaborines is leveraged to achieve regioselective mono- and difunctionalization at all four carbon positions. The installed functionalities are subsequently translated into cyclobutane β-amino alcohol frameworks through a tandem photoisomerization-hydrogenation-oxidation sequence. This strategy provides access to eight distinct substitution patterns with high levels of modularity and diastereoselectivity.
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