Journal
ORGANIC LETTERS
Volume 22, Issue 4, Pages 1340-1344Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b04652
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Funding
- CSIR
- UGC
- CSIR-IICB
- Bristol-Myers Squibb (USA)
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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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