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Diastereoselective Synthesis of Pentasubstituted γ-Butyrolactones from Silyl Glyoxylates and Ketones through a Double Reformatsky Reaction

✍ Scribed by Stephen N. Greszler; Jeffrey S. Johnson

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
323 KB
Volume
48
Category
Article
ISSN
0044-8249

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✦ Synopsis

Abstract

Three contiguous stereocenters can be established with remarkable diastereoselectivity in a double Reformatsky sequence. Densely functionalized γ‐butyrolactones were assembled rapidly by this approach, in which a ketone is used as the terminal electrophile (see scheme). Secondary transformations of the lactone products enhance their synthetic utility. R^1^=Me, H; R^2^=alkyl, aryl, CF~3~; Bn=benzyl, TBS=tert‐butyldimethylsilyl.magnified image

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