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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.