Premium
Total Synthesis of ( R , R , R )‐α‐Tocopherol Through Asymmetric Cu‐Catalyzed 1,4‐Addition
Author(s) -
Termath Andreas Ole,
Sebode Hanna,
Schlundt Waldemar,
Stemmler René T.,
Netscher Thomas,
Bonrath Werner,
Schmalz HansGünther
Publication year - 2014
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.201404379
Subject(s) - phosphoramidite , tocopherol , stereoselectivity , substituent , catalysis , chemistry , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , antioxidant , vitamin e , dna , biochemistry , oligonucleotide
By introducing a disposable activating substituent at C‐3, the asymmetric 1,4‐addition to a notoriously unreactive 2‐substituted chromenone was achieved with high levels of (2 R )‐stereoselectivity in the presence of a chiral Cu I ‐phosphoramidite complex as a catalyst. This paved the way for an efficient and conceptually novel synthesis of ( R , R , R )‐α‐tocopherol from readily available starting materials.
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