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Stereoselective Synthesis of 3,5‐Dihydroxypyrrolidin‐2‐ones Through a Photoinduced Multicomponent Reaction Followed by Dimerization
Author(s) -
Bergamaschi Enrico,
Capurro Pietro,
Lambruschini Chiara,
Riva Renata,
Basso Andrea
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901080
Subject(s) - chemistry , stereoselectivity , aldol reaction , adduct , combinatorial chemistry , stereochemistry , organic chemistry , catalysis
A photoinduced reaction between diazoketones, isocyanides and silanols, followed by aldol dimerization of the resulting multicomponent adduct, affords polyfunctionalized 3,5‐dihydroxypyrrolidin‐2‐one heterocycles in a straightforward manner. Six new bonds and two quaternary carbons are formed in just two steps with this complexity‐generating methodology. A high degree of stereoselectivity is also observed, as a result of the mild conditions employed. Moreover, the 3,5‐dihydroxypyrrolidin‐2‐one scaffold can be found in two families of biologically relevant natural products, namely anchinopeptolides and eusynstyelamides. The synthetic approach herein described appears to be a very convenient route for the preparation of their analogues.