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Organocuprate‐Initiated Domino Michael–Intramolecular Aldol Reaction – Application to the Formation of Ring B of the Aglycon of Landomycins
Author(s) -
Bugaut Xavier,
Roulland Emmanuel
Publication year - 2012
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.201101766
Subject(s) - aldol reaction , intramolecular force , domino , michael reaction , chemistry , stereochemistry , ring (chemistry) , combinatorial chemistry , organic chemistry , catalysis
An innovative access to a β,β‐disubstituted Morita–Baylis–Hillman motif, which is a potential intermediate en route to the synthesis of the aglycon of landomycins, is presented. It consists of a finely optimized organocuprate‐initiated domino Michael–intramolecular aldol reaction. The use of TMSCl and DMAP as additives proved essential to ensure the success of this reaction sequence.