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

Greszler Stephen N. | Zendy; Johnson Jeffrey S. | Zendy

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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.

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