Diastereo- and Enantioselective Pd(II)-Catalyzed Additions of 2‑Alkylazaarenes to N‑Boc Imines and Nitroalkenes

Diastereo- and Enantioselective Pd(II)-Catalyzed Additions of 2‑Alkylazaarenes to N‑Boc Imines and Nitroalkenes

A chiral Pd(II)–bis(oxazoline) complex was found to be highly effective in promoting the first direct diastereo- and enantioselective addition of alkyl­aza­arenes to N-Boc aldimines and nitroalkenes under mild conditions. Deprotection of Boc-protected products proceeded readily to provide amines in...

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Veröffentlicht in:Journal of the American Chemical Society 2012-11, Vol.134 (44), p.18193-18196
Hauptverfasser: Best, Daniel, Kujawa, Szymon, Lam, Hon Wai
Format: Artikel
Sprache:eng
Schlagworte:
Alkenes - chemical synthesis
Alkenes - chemistry
Aza Compounds - chemical synthesis
Aza Compounds - chemistry
Catalysis
Hydrocarbons, Aromatic - chemical synthesis
Hydrocarbons, Aromatic - chemistry
Imines - chemical synthesis
Imines - chemistry
Nitro Compounds - chemical synthesis
Nitro Compounds - chemistry
Oxazoles - chemistry
Palladium - chemistry
Stereoisomerism
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Zusammenfassung:A chiral Pd(II)–bis(oxazoline) complex was found to be highly effective in promoting the first direct diastereo- and enantioselective addition of alkyl­aza­arenes to N-Boc aldimines and nitroalkenes under mild conditions. Deprotection of Boc-protected products proceeded readily to provide amines in high yields.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja3083494