Premium
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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom