Oxazolidine Sulfur Ylides Derived from Phenylglycinol for the Specific and Highly Diastereoselective Synthesis of Aryl and Alkyl trans‐Epoxyamides. Issue 25 (19th July 2013)

• Record Type: Journal Article
• Authors: Gordillo, Paola G.; Aparicio, David M.; Flores, Marcos; Mendoza, Angel; Orea, Laura; Juárez, Jorge R.; Huelgas, Gabriela; Gnecco, Dino; Terán, Joel L.
• Is Part Of: European journal of organic chemistry. Issue 25(2013)
• Page Start: 5561
• Page End: 5565
• Publication Date: 2013-07-19
• Subjects: Sulfur -- Ylides -- Asymmetric synthesis -- Epoxidation -- Diastereoselectivity; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201300732
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : A highly diastereoselective method for the synthesis of a series of aliphatic and aromatic trans ‐epoxyamides from chiral cis ‐ and trans ‐sulfonium salts derived from (–)‐( R )‐2‐phenylglycinol is accomplished. The diastereoselective outcome depends on the stereochemistry of the chiral center at the C‐4 position of the oxazole moiety.