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A Protecting‐Group‐Free Route to Chiral BINOL–Phosphoric Acids
Author(s) -
Li Baojian,
Chiu Pauline
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100328
Subject(s) - chemistry , phosphoric acid , protecting group , suzuki reaction , combinatorial chemistry , group (periodic table) , coupling (piping) , organic chemistry , catalysis , palladium , mechanical engineering , alkyl , engineering
A two‐step, protecting group‐free route for the synthesis of 3,3′‐disubstituted and 6,6′‐disubstituted chiral BINOL–phosphoric acids has been realized starting from commercially available brominated BINOLs. This synthesis relies on the direct Suzuki coupling of brominated BINOL phosphoric acids. This synthetic strategy is more efficient compared to previous circuitous strategies involving protections and deprotections, and the process is higher yielding relative to the alternative two‐step synthesis involving Suzuki coupling of the BINOL.