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. 2016 Feb 5;81(3):1295-9.
doi: 10.1021/acs.joc.5b02663. Epub 2016 Jan 7.

Gram Scale Conversion of R-BINAM to R-NOBIN

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Gram Scale Conversion of R-BINAM to R-NOBIN

Darshan C Patel et al. J Org Chem. .
Free article


A mild, operationally simple, and single-step transition-metal-free protocol for the synthesis of enantiomerically pure (R)-(+)-2'-amino-1,1'-binaphthalen-2-ol (R-NOBIN) from (R)-(+)-1,1'-binaphthyl-2,2'-diamine (R-BINAM) is reported. The one-pot conversion proceeds with good yield and shows no racemization. The hydroxyl on the R-NOBIN product was shown to have come from water in the reaction medium via an H2(18)O study. The correct value of the specific rotation of R-NOBIN was reported.

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