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Oxazolidine Sulfur Ylides Derived from Phenylglycinol for the Specific and Highly Diastereoselective Synthesis of Aryl and Alkyl trans ‐Epoxyamides
Author(s) -
Gordillo Paola G.,
Aparicio David M.,
Flores Marcos,
Mendoza Angel,
Orea Laura,
Juárez Jorge R.,
Huelgas Gabriela,
Gnecco Dino,
Terán Joel L.
Publication year - 2013
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.201300732
Subject(s) - chemistry , oxazolidine , oxazole , sulfonium , moiety , alkyl , aryl , stereochemistry , methanesulfonic acid , organic chemistry , salt (chemistry)
Aryl and alkyl chiral oxazolidine sulfonium salts with cis and trans dispositions derived from (–)‐( R )‐2‐phenylglycinol were demonstrated to be good to excellent chiral auxiliaries for the diastereoselective synthesis of (2 R ,3 S )‐ trans ‐epoxyamides. Interestingly, the diastereoselective outcome depends on the stereochemistry of the chiral center at the C‐4 position of the oxazole moiety. The stereoselectivities were consistent even for aliphatic aldehydes.