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Diastereoselective synthesis of pentasubstituted gamma-butyrolactones from silyl glyoxylates and ketones through a double Reformatsky reaction

Diastereoselective synthesis of pentasubstituted gamma-butyrolactones from silyl glyoxylates and ketones through a double Reformatsky reaction

Angewandte Chemie 48(20): 3689-3691

Three contiguous stereocenters can be established with remarkable diastereoselectivity in a double Reformatsky sequence. Densely functionalized gamma-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.

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Accession: 052591919

Download citation: RISBibTeXText

PMID: 19373816

DOI: 10.1002/anie.200900215

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