Diastereoselective synthesis of pentasubstituted gamma-butyrolactones from silyl glyoxylates and ketones through a double Reformatsky reaction.
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.
Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, NC 27599, USA.
Stephen N
SN
Greszler
Jeffrey S
JS
Johnson
D015107:4-Butyrolactone / Q000138:chemical synthesis*; D006038:Glyoxylates / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D013237:Stereoisomerism
D006038:Glyoxylates; D007659:Ketones; C031150:glyoxylic acid; D015107:4-Butyrolactone