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1,3‐Dipolar Cycloaddition of Azomethine Ylides to Aldehydes: Synthesis of anti α‐Amino‐β‐Hydroxy Esters
Author(s) -
Danielsson Jakob,
Toom Lauri,
Somfai Peter
Publication year - 2011
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.201001274
Subject(s) - chemistry , azomethine ylide , cycloaddition , diastereomer , hydrolysis , 1,3 dipolar cycloaddition , organic chemistry , ring (chemistry) , amino esters , aldehyde , catalysis
A 1,3‐dipolar cycloaddition reaction of azomethine ylides to aldehydes is described. The azomethine ylides, generated by thermal electrocyclic ring opening of aziridines, adds to aldehydes in good yields with moderate to good selectivities to furnish oxazolidines. The oxazolidines were subsequently hydrolyzed to the corresponding amino alcohols, giving the anti diastereomer as the major product.