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Kinetic Resolution of Unprotected BINOLs via Lewis Base-Catalyzed O-Boc Protection
Zhe Xu1, Hongwei Zhou2, Xingkuan Chen3
1School of Chemistry and Chemical Engineering, Zhejiang Sci-Tech University, Hangzhou 310018, P. R. China.
Abstract:
A Lewis base-catalyzed kinetic resolution of 1,1'-bi-2,2'-naphthols (BINOLs) through atroposelective O-Boc protection is described. Using a commercially available biscinchona alkaloid catalyst, a broad range of unprotected BINOLs undergo selective transformation with Boc anhydride (Boc2O) to deliver enantioenriched BINOLs with selectivity factors (s) up to 78. The resulting enantioenriched BINOLs can be further diversified by transition-metal-catalyzed cross-coupling reactions, providing streamlined access to structurally varied BINOL analogs.
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