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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
121
Category
Article
ISSN
0044-8249

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✦ Synopsis

Abstract

Drei benachbarte Stereozentren werden in einer bemerkenswert diastereoselektiven doppelten Reformatsky‐Sequenz erzeugt. Dieser Ansatz, bei dem ein Keton als abschließendes Elektrophil dient, lieferte sehr rasch hoch funktionalisierte γ‐Butyrolactone (siehe Schema), die für zahlreiche Folgereaktionen geeignet sind. R^1^=Me, H; R^2^=Alkyl, Aryl, CF~3~; Bn=Benzyl, TBS=tert‐Butyldimethylsilyl.magnified image

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