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A Chiral Building Block for the Stereocontrolled Installation of the 1,3‐Diol Motif (Eur. J. Org. Chem. 2/2016)
Author(s) -
Bredenkamp Angela,
Zhu ZhiBin,
Kirsch Stefan F.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201690002
Subject(s) - stereocenter , block (permutation group theory) , chemistry , diol , diastereomer , stereochemistry , simple (philosophy) , aldehyde , combinatorial chemistry , combinatorics , enantioselective synthesis , organic chemistry , mathematics , catalysis , philosophy , epistemology
The cover picture shows a newly developed building block, which gives a simple and flexible access to 1,3‐diols as demonstrated in the Communication by S. F. Kirsch et al. on p. 252 ff . This building block is chiral, and the stereogenic center that is part of the building block is unambiguously fixed. Attaching the building block to an aldehyde through olefination followed by substrate‐directed reduction then allows for the stereocontrolled creation of a 1,3‐diol unit. For example, both diastereomers of the naturally occurring 1,2,4‐trihydroxynonadecane, isolated from the unripe avocado fruit, can be synthesized in a stereocontrolled way by using this building block: One compound to create them all ...