Premium
Benzoxaborole Catalyst for Site‐Selective Modification of Polyols
Author(s) -
Kusano Shuhei,
Miyamoto Shoto,
Matsuoka Aki,
Yamada Yuji,
Ishikawa Ryuta,
Hayashida Osamu
Publication year - 2020
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.201901749
Subject(s) - chemistry , substituent , selectivity , catalysis , trifluoromethyl , combinatorial chemistry , protecting group , diol , organic chemistry , alkyl
The site‐selective modification of polyols bearing several hydroxyl groups without the use of protecting groups remains a significant challenge in synthetic chemistry. To address this problem, novel benzoxaborole derivatives were designed as efficient catalysts for the highly site‐selective and protecting‐group‐free modification of polyols. To identify the effective substituent groups enhancing the catalytic activity and selectivity, a series of benzoxaborole catalysts 1a – k were synthesized. In‐depth analysis for the substituent effect revealed that 1i – k , bearing multiple electron‐withdrawing fluoro‐ and trifluoromethyl groups, exhibited the greatest catalytic activity and selectivity. Moreover, 1i ‐catalyzed benzoylation, tosylation, benzylation, and glycosylation of various cis‐1,2‐diol derivatives proceeded with good yield and site‐selective manner.