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ChemInform Abstract: Enantiomerically Pure 3-Substituted 2-Phenylprolines by Caesium Fluoride/Tetramethoxysilane Mediated 1,4-Addition of (3S,5R)- Diphenylmorpholin-2-one to Acrylates.

โœ Scribed by L. M. HARWOOD; G. HAMBLETT; A. I. JIMENEZ-DIAZ; D. J. WATKIN

Publisher
John Wiley and Sons
Year
2010
Weight
34 KB
Volume
28
Category
Article
ISSN
0931-7597

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โœฆ Synopsis

Enantiomerically Pure 3-Substituted 2-Phenylprolines by Caesium Fluoride/Tetramethoxysilane Mediated 1,4-Addition of (3S,5R)-Diphenylmorpholin-2-one to Acrylates.

-In continuation of the asymmetric synthesis of nonproteinogenic amino acids, the silane-mediated 1,4-addition of acrylates (II) to the chiral 3,5-disubstituted morpholine (I) and the TFA-promoted cyclization of the resulting adducts (III) to lactams (IV)/(V) are described. The major isomers (cf. (IVb)) may be converted to enantiopure ฮฑ-phenyl prolines (VII). -(

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โœ E. P. SCHREINER; A. PRUCKNER ๐Ÿ“‚ Article ๐Ÿ“… 2010 ๐Ÿ› John Wiley and Sons โš– 37 KB ๐Ÿ‘ 1 views

Syn-Selective Michael Addition of Amines to Bis-enones: Synthesis of 1, 3,4,7-Tetrasubstituted (4R,5S,6S,7R)-Hexahydro-5,6-dihydroxy-2H-1,3-diazepin-2-ones. -The O-protected title compounds (IX), seven-membered cyclic ureas, are useful as intermediates in the synthesis of HIV-proteinase inhibitors.