Open AccessBiotin – The Chiral Challenge
Author(s) -
Werner Bonrath,
Reinhard Karge,
Thomas Netscher,
Felix Roessler,
Felix Spindler
Publication year - 2009
Publication title -
chimia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.387
H-Index - 55
eISSN - 2673-2424
pISSN - 0009-4293
DOI - 10.2533/chimia.2009.265
Subject(s) - enantioselective synthesis , catalysis , reagent , combinatorial chemistry , yield (engineering) , homogeneous , chemistry , organic chemistry , materials science , mathematics , combinatorics , metallurgy
In this contribution, the first examples of the catalytic highly enantioselective reduction of cyclic meso-anhydrides to lactones and of thioanhydrides to thiolactones are described. The N-benzyl protected key building blocks in the industrial synthesis of (+)-biotin were so far only accessible by usage of expensive reagents in multi-step procedures. In contrast, homogeneous catalytic enantioselective hydrogenation of the corresponding meso-anhydride mediated by a metal phosphane complex proceeds with high optical induction (ee >95%) and excellent yield. The catalytic system provides a generally applicable new method for the preparation of lactones from cyclic anhydrides.