AI Article Synopsis
- A new method using Rh(III) catalysis has been developed to create spirocycles by combining benzoxazines with nitroolefins through C-H functionalization.
- The reaction efficiently builds three stereogenic centers in a single step from easily obtainable achiral materials and uses mild conditions.
- This process results in a variety of pharmaceutically important nitro-substituted spirocyclic 2,3-dihydro-1,4-benzoxazine derivatives, achieving high yields and selectivity.
Article Abstract
A Rh(III)-catalyzed [3 + 2] annulation of benzoxazines with nitroolefins that proceeds via redox-neutral C-H functionalization has been demonstrated, leading to the novel class of spirocycles in a single step. The construction of three continuous stereogenic centers has been achieved starting from easily accessible achiral substrates in an atom-efficient manner under mild reaction conditions. A broad range of pharmaceutically relevant nitro substituted spirocyclic 2,3-dihydro-1,4-benzoxazine derivatives has been synthesized in good to excellent yields with high diastereoselectivity.
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| http://dx.doi.org/10.1021/acs.orglett.9b04652 | DOI Listing |
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