An improved synthesis of optically pure 4-boc-5,6-diphenylmorpholin-2-one and 4-cbz-5,6-diphenylmorpholin-2-one

A convenient synthesis of optically pure 4-Boe-5,6-diphenylmorpholin-2-one and 4-Cbz-5,6-diphenylmorpholin-2-one by reaction of (+)- or (-)-2-amino-1,2-diphenylethanol with ethyl bromoacetate, followed by N-protection, and p-TsOH-mediated ring-closure is described. The title compounds can be used as...

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Bibliographic Details
Published inSynlett no. 4; pp. 693 - 696
Main Authors Dastlik, KA, Sundermeier, U, Johns, DM, Chen, Y, Williams, RM
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 04.03.2005
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CONCISE
lactones
asymmetric synthesis
2-amino-1,2-diphenylethanol
ring-closure
amino acids
STEREOCHEMISTRY
RESOLUTION
ALPHA-AMINO-ACIDS
STEREOSELECTIVE-SYNTHESIS
TETRAZOMINE
ASYMMETRIC TOTAL-SYNTHESIS
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Summary:A convenient synthesis of optically pure 4-Boe-5,6-diphenylmorpholin-2-one and 4-Cbz-5,6-diphenylmorpholin-2-one by reaction of (+)- or (-)-2-amino-1,2-diphenylethanol with ethyl bromoacetate, followed by N-protection, and p-TsOH-mediated ring-closure is described. The title compounds can be used as synthons for the asymmetric synthesis of N-protected alpha-amino acids. These lactones are quite stable to storage and handling.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2005-863740