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Diastereoselective Synthesis of Pentasubstituted γ‐Butyrolactones from Silyl Glyoxylates and Ketones through a Double Reformatsky Reaction
Author(s) -
Greszler Stephen N.,
Johnson Jeffrey S.
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200900215
Subject(s) - reformatsky reaction , chemistry , electrophile , ketone , stereocenter , silylation , lactone , alkyl , stereochemistry , aryl , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis
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.