Gram Scale Conversion of R-BINAM to R-NOBIN

作者：Patel Darshan C; Breitbach Zachary S; Woods Ross M; Lim Yeeun; Wang Andy; Foss Frank W Jr; Armstrong Daniel W^*

来源：Journal of Organic Chemistry, 2016, 81(3): 1295-1299.

DOI：10.1021/acs.joc.5b02663

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 (H2O)-O-18 study. The correct value of the specific rotation of R-NOBIN was reported.

• 出版日期2016-2-5