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Neighboring Lithium‐Assisted [1,2]‐Wittig Rearrangement: Practical Access to Diarylmethanol‐Based 1,4‐Diols and Optically Active BINOL Derivatives with Axial and sp 3 ‐Central Chirality
Author(s) -
Gao Guang,
Gu FengLei,
Jiang JianXiong,
Jiang Kezhi,
Sheng ChunQi,
Lai GuoQiao,
Xu LiWen
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201003111
Subject(s) - optically active , chirality (physics) , lithium (medication) , wittig reaction , axial chirality , chemistry , combinatorial chemistry , materials science , stereochemistry , catalysis , enantioselective synthesis , physics , organic chemistry , biology , particle physics , chiral symmetry breaking , endocrinology , nambu–jona lasinio model , quark
A facile and practical methodology for the synthesis of synthetically useful diarylmethanol‐based 1,4‐diols and enantiomerically pure BINOL‐derived diols with axial and sp 3 ‐central chirality has been developed through neighboring lithium‐promoted [1,2]‐Wittig rearrangement. The chirality transfer process shows a broad substrate scope in terms of the aromatic ether substituent, which allows access to a broad of range of chiral 1,1′‐binaphthalene‐2‐α‐arylmethanol‐2′‐ols with excellent enantioselectivities (>99 % enantiomeric excess) and yields (84–96 %). This should be considered as an available and attractive chiral source to design and prepare privileged ligands or catalysts.