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An Enantioselective Synthesis of ( R )‐5,6‐Octadecadienoic Acid
Author(s) -
Yu Qiong,
Ma Shengming
Publication year - 2015
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.201403588
Subject(s) - enantioselective synthesis , chemistry , allene , propargyl , propargyl alcohol , enantiomeric excess , total synthesis , chirality (physics) , enantiomer , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark
A convenient, scalable, and highly enantioselective total synthesis of ( R )‐5,6‐octadecadienoic acid was developed by using the recently established ATA (allenylation of terminal alkynes) reaction of TBS‐protected (TBS = tert ‐butyldimethylsilyl) propargyl alcohol with n ‐dodecanal in the presence of ( R )‐α,α‐diphenylprolinol as the chiral source. The axial chirality of the allene unit withstood the many common organic transformations that were needed to achieve the total synthesis with a high ee (enantiomeric excess) value.