1998
DOI: 10.1021/jo9807565
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Synthesis of N-Alkylated and N-Arylated Derivatives of 2-Amino-2‘-hydroxy-1,1‘-binaphthyl (NOBIN) and 2,2‘-Diamino-1,1‘-binaphthyl and Their Application in the Enantioselective Addition of Diethylzinc to Aromatic Aldehydes

Abstract: High-yield reductive alkylation of (R)-(+)-1 and (R)-(+)-2 has been accomplished with a series of ketones (even as bulky as 2-adamantanone) and NaBH 4 /H 2 SO 4 in THF at room temperature to give the respective N-alkylated binaphthyls 6a-c, 9a-c, and 10a-c. Related N-phenyl derivatives 14, 16, and 17 were obtained via the Pd(0)-catalyzed coupling of (R)-(+)-1 and (R)-(+)-2, respectively, with PhBr; no racemization was observed. Subsequent reductive methylation with CH 2 O and NaBH 4 /H 2 SO 4 afforded the bide… Show more

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Cited by 130 publications
(46 citation statements)
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“…Anhydrous YbCl 3 and YCl 3 and (R)-(+)-1,1'-binaphthyl-2,2'-diamine were purchased. Compounds Y[NA C H T U N G T R E N N U N G (tms) 2 ] 3 , [26] (R)-(+)-2,2'-Bis(cyclopentylamino)-1,1'-binaphthyl, [27] and Ph 2 CHK [28] were prepared according to reported procedures. The bis(N-neopentyl)binaphthylamine ligand and the complex Li…”
Section: Methodsmentioning
confidence: 99%
See 1 more Smart Citation
“…Anhydrous YbCl 3 and YCl 3 and (R)-(+)-1,1'-binaphthyl-2,2'-diamine were purchased. Compounds Y[NA C H T U N G T R E N N U N G (tms) 2 ] 3 , [26] (R)-(+)-2,2'-Bis(cyclopentylamino)-1,1'-binaphthyl, [27] and Ph 2 CHK [28] were prepared according to reported procedures. The bis(N-neopentyl)binaphthylamine ligand and the complex Li…”
Section: Methodsmentioning
confidence: 99%
“…Anhydrous YbCl 3 and YCl 3 and ( R )‐(+)‐1,1′‐binaphthyl‐2,2′‐diamine were purchased. Compounds Y[N(tms) 2 ] 3 ,26 (R )‐(+)‐2,2′‐Bis(cyclopentylamino)‐1,1′‐binaphthyl,27 and Ph 2 CHK28 were prepared according to reported procedures. The bis( N ‐neopentyl)binaphthylamine ligand and the complex Li‐ 3 d [Li(thf) 4 ][Yb{( R )‐ 20 H 12 N 2 (C 5 H 11 )} 2 ] were prepared according to the procedure we previously described 20.…”
Section: Methodsmentioning
confidence: 99%
“…The same research group has published application of conformationally flexible 1‐trityloxymethyl‐ and 2‐trityloxymethyl‐2‐aminoethanol derivatives as efficient ligands for diethylzinc additions to benzaldehydes, and the usefulness of aminoindanol isomers in different enantioselective catalytic reactions . Despite the huge success of axially chiral ligands in asymmetric synthesis, only a few examples of amino alcohols with 1,1′‐biaryl backbone (atropisomeric phenol or naphthol derivatives) are reported for the addition of organozincs to aldehydes . In most cases, the catalytic activity of the new ligand‐dialkylzinc complexes and the result (yield and enantiomeric excess, ee ) of the test reaction (addition of diethylzinc to benzaldehyde) are only reported and fewer studies have been directed to correlate the structural factors with catalytic activities .…”
Section: Introductionmentioning
confidence: 99%
“…Diethylzinc (DEZn), a reactive compound, has usually been used as an efficient catalyst in organic reactions such as epoxide polymerization,22, 23 reduction of aldehydes and ketones,24, 25 and as reactants for conjugate addition reactions 26. In addition, doping magnetic nanoparticles and semiconductor nanowires by DEZn to adjust their properties have also been reported 27–29.…”
Section: Introductionmentioning
confidence: 99%