Acid-Catalyzed [3,3] Sigmatropic Rearrangement of N-Cbz-Diaryl Hydrazide for the Synthesis of Mono-N-Cbz-1,1′-biaryl-2,2′-diamine

N‐Cbz‐Diaryl hydrazides undergo acid‐catalyzed [3,3] sigmatropic rearrangement to afford N‐Cbz‐1,1′‐biaryl‐2,2′‐diamines. The resultant products can be versatile synthetic platforms for a wide variety of C2‐ and/or nonsymmetric axially chiral ligands and organocatalysts. N‐Cbz‐Diaryl hydrazides bear...

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Veröffentlicht in:European Journal of Organic Chemistry 2011-01, Vol.2011 (3), p.455-457
Hauptverfasser: Suh, Sung-Eun, Park, In-Keol, Lim, Byeong-Yun, Cho, Cheon-Gyu
Format: Artikel
Sprache:eng
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Zusammenfassung:N‐Cbz‐Diaryl hydrazides undergo acid‐catalyzed [3,3] sigmatropic rearrangement to afford N‐Cbz‐1,1′‐biaryl‐2,2′‐diamines. The resultant products can be versatile synthetic platforms for a wide variety of C2‐ and/or nonsymmetric axially chiral ligands and organocatalysts. N‐Cbz‐Diaryl hydrazides bearing either a neutral or electron‐donating group underwent highly efficient acid‐catalyzed [3,3] sigmatropic rearrangement to afford N‐Cbz‐1,1′‐biaryl‐2,2′‐diamines. The resultant products allow elaboration of various new C2‐ and/or nonsymmetric axially chiral ligands or organocatalysts.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201001461