A facile synthesis of the enantiopure, nitrogen-substituted 2,2 '-diamino-1,1 '-binaphthyls as potential ligands for catalytic asymmetric reactions

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 bully 2-adamantanone afforde...

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Bibliographic Details
Published inCollection of Czechoslovak chemical communications Vol. 63; no. 4; pp. 515 - 519
Main Authors Vyskocil, S, Smrcina, M, Kocovsky, P
Format Journal Article
LanguageEnglish
Published PRAGUE 6 Inst Organic Chem And Biochem 1998
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
axial chirality
binaphthyls
palladium catalysis
biaryls
PALLADIUM COMPLEXES
2-AMINO-2'-HYDROXY-1,1'-BINAPHTHYL
AMINES
HYDROSILYLATION
amine arylation
amine reductive alkylation
chiral ligands
DERIVATIVES
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Summary: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 bully 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(O)-catalyzed phenylation of (R)-(+)-1 with PhBr afforded the N,N'-diphenyl derivative (R)-7 (70%).
ISSN:0010-0765
DOI:10.1135/cccc19980515