General asymmetric synthesis of hydroxymethylene and hydroxyethylene peptide isosteres
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Add time:08/30/2019 Source:sciencedirect.com
The Lewis acid-promoted coupling reactions of (5R, 6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazines (11a-e, and 21), which are prepared easily from (+-(5R, 6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (9), with allyltrimethylsilane proceeded to give the corresponding coupling products with moderate to excellent stereoselectivity in good yields. These coupling products (13a, b, and d) were converted to hydroxymethylene- (25a, b, and d) and hydroxyethylene (28) peptide isosteres.
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