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1. Total synthesis of (R,R,R)-α-tocopherol through asymmetric Cu-catalyzed 1,4-addition.

Author

Termath AO, Sebode H, Schlundt W, Stemmler RT, Netscher T, Bonrath W, and Schmalz HG

Subjects
Catalysis, Molecular Structure, Stereoisomerism, alpha-Tocopherol chemistry, Copper chemistry, alpha-Tocopherol chemical synthesis
Abstract

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 (2R)-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., (© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Published
2014
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