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Allylsilanes in organic synthesis; stereoselective synthesis of trans-alkene peptide isosteres

โœ Scribed by Matthew J. Daly; Richard A. Ward; David F. Thompson; Garry Procter


Publisher
Elsevier Science
Year
1995
Tongue
French
Weight
247 KB
Volume
36
Category
Article
ISSN
0040-4039

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A general synthetic route to trans-alkene isosteres of protected dipeptides is reported. This sequence permits the fully stereocontrolled preparation of these isosteres in optically active form and in quantities sufficient for further biological study. Prepared in this manner were alkene isosteres o

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The ester-allylsilanes ( 5) and ( 6) and the acid-allylsilane (7) react stereoselectively with m-CPBA; the major product from ( 5) and ( 7) was the y-lactone (4), whereas (6) failed to undergo lactonisation, the major product in this case was the P,wpoxy-silane (12).