N-Substituted Amides as Chiral Ligands for Catalytic Asymmetric Reactions

2002 ◽  
Vol 6 (10) ◽  
pp. 865-890 ◽  
Author(s):  
Ji Zhang ◽  
Hai-Bing Zhou ◽  
Ru-Gang Xie
Author(s):  
Sara Meninno ◽  
Francesca Franco ◽  
Maurizio Benaglia ◽  
Alessandra Lattanzi

1998 ◽  
Vol 63 (4) ◽  
pp. 515-519 ◽  
Author(s):  
Štěpán Vyskočil ◽  
Martin Smrčina ◽  
Pavel Kočovský

Reductive alkylation of (R)-(+)-2,2'-diamino-1,1'-binaphthyl (1) with various ketones has been accomplished by means of NaBH4/H2SO4 in THF at room temperature. Bisalkylation predominated with the sterically less demanding acetone (1→3a; 82%), whereas the bulky 2-adamantanone afforded mainly the monoalkylated product 4c (71%). Both mono- and bisalkylated diamines (R)-3 and (R)-4 were reductively permethylated on reaction with CH2O, NaBH4, and H2SO4. The Pd(0)-catalyzed phenylation of (R)-(+)-1 with PhBr afforded the N,N'-diphenyl derivative (R)-7 (70%).


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